YU46663B - PROCESS FOR THE PREPARATION OF CRYSTAL N- (S-3-ALKYL-HEPTANOYL) -D-GAMA-GLUTAMYL-GLYCYL-D-ALANINE - Google Patents
PROCESS FOR THE PREPARATION OF CRYSTAL N- (S-3-ALKYL-HEPTANOYL) -D-GAMA-GLUTAMYL-GLYCYL-D-ALANINEInfo
- Publication number
- YU46663B YU46663B YU155987A YU155987A YU46663B YU 46663 B YU46663 B YU 46663B YU 155987 A YU155987 A YU 155987A YU 155987 A YU155987 A YU 155987A YU 46663 B YU46663 B YU 46663B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- methyl
- alkyl
- formula
- compound
- double bond
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 abstract 2
- RFYQVSFBWCSKGJ-GJIOHYHPSA-N (e,3r)-3-ethylhept-4-enoic acid Chemical compound CC\C=C\[C@H](CC)CC(O)=O RFYQVSFBWCSKGJ-GJIOHYHPSA-N 0.000 abstract 1
- XRWMJTDFZGUSLR-KPJROHGDSA-N (e,3r)-3-methylhept-4-enoic acid Chemical compound CC\C=C\[C@H](C)CC(O)=O XRWMJTDFZGUSLR-KPJROHGDSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 230000001419 dependent effect Effects 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
POSTUPAK ZA DOBIJANJE KRISTALNOG N-(S-3-ALKIL-HEPTANOIL)-D-GAMA-GLUTAMIL-GLICIL-D-ALANINA, a drugi je (C1-C6)alkil ili (C6-C8)cikloalkilmetil, naznačen t ime, što obuhvata fazu kuplovanja aktiviranog oblika R-trans-3-metil-4-heptenske kiseline, R-trans-3-etil-4- heptenske kiseline ili S-3-metil-6-heptenske kiseline sa jedinjenjem apsolutne stereohemijske formule pri čemu R6 i R7 su svaki benzil ili jedan R6 i R7 je benzil, a drugi je (C1-C6)alkil ili (C6-C8)cikloalkil-metil radi formiranja jedinjenja apsolutne stereohemijske formule pri čemu jedna ili druga, ali ne obe tačkaste linije predstavljaju dvostruku vezu, R je metil ili etil pod uslovom da kada je dvostruka veza u terminalnom 6,7-položaju R je metil i fazu hidrogenovanja jedinjenja formule (IIIc) radi formiranja jedinjenja formule (I) sa uporednom reakcijom dvostruke veze i hidrogenolizom benzilestarske grupe, kao i kristalizaciju jedinjenja formule (I) u kojoj je R metil, a R4 i R5 su vodonik, iz organskog rastvarača ili grupe rastvarača. Prijava sadrži još 1 zavisan zahtev.A process for the production of CRYSTAL N- (S-3-ALKYL-HEPTANOYL) -D-GAMA-GLUTAMYL-GLYCYL-D-ALANINE, the other being (C1-C6) alkyl or (C6-C8) cycloalkylmethyl, indicated by the name comprising the coupling step of an activated form of R-trans-3-methyl-4-heptenic acid, R-trans-3-ethyl-4-heptenic acid or S-3-methyl-6-heptenic acid with a compound of absolute stereochemical formula wherein R6 and R7 is each benzyl or one R6 and R7 is benzyl and the other is (C1-C6) alkyl or (C6-C8) cycloalkyl-methyl to form compounds of absolute stereochemical formula wherein one or the other but not both dotted lines represent a double bond , R is methyl or ethyl provided that when the double bond is in the terminal 6,7-position R is methyl and the hydrogenation phase of a compound of formula (IIIc) to form a compound of formula (I) with a parallel double bond reaction and hydrogenolysis of a benzyl ester group, as well as crystallization of a compound of formula (I) wherein R is methyl and R 4 and R 5 are hydrogen, from an organic solvent or group is a solvent. The application contains 1 more dependent request.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1986/001775 WO1988001613A1 (en) | 1986-08-27 | 1986-08-27 | Crystalline n-(s-3-methylheptanoyl)-d-gamma-glutamyl-glycyl-d-alanine, and processes and intermediates therefor |
| PCT/US1986/001772 WO1988001612A1 (en) | 1986-08-27 | 1986-08-27 | Processes and intermediates for n-(s-3-alkyl-heptanoyl)-d-gamma-glutamyl-glycyl-d-alanine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU155987A YU155987A (en) | 1989-02-28 |
| YU46663B true YU46663B (en) | 1994-01-20 |
Family
ID=26773904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU155987A YU46663B (en) | 1986-08-27 | 1987-08-24 | PROCESS FOR THE PREPARATION OF CRYSTAL N- (S-3-ALKYL-HEPTANOYL) -D-GAMA-GLUTAMYL-GLYCYL-D-ALANINE |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPH0637517B2 (en) |
| KR (1) | KR900004106B1 (en) |
| CN (1) | CN1021436C (en) |
| DK (1) | DK444887A (en) |
| EG (1) | EG18303A (en) |
| IL (1) | IL83657A (en) |
| MY (1) | MY101823A (en) |
| NZ (1) | NZ221570A (en) |
| PH (1) | PH27397A (en) |
| PL (1) | PL156175B1 (en) |
| PT (1) | PT85581B (en) |
| YU (1) | YU46663B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113548977A (en) * | 2021-07-12 | 2021-10-26 | 广州乐信生物科技有限公司 | Process for producing N-methyl-beta-alanine derivative |
-
1987
- 1987-08-13 EG EG467/87A patent/EG18303A/en active
- 1987-08-24 YU YU155987A patent/YU46663B/en unknown
- 1987-08-25 PT PT85581A patent/PT85581B/en not_active IP Right Cessation
- 1987-08-25 PL PL1987267444A patent/PL156175B1/en unknown
- 1987-08-25 MY MYPI87001442A patent/MY101823A/en unknown
- 1987-08-26 IL IL83657A patent/IL83657A/en not_active IP Right Cessation
- 1987-08-26 DK DK444887A patent/DK444887A/en not_active Application Discontinuation
- 1987-08-26 NZ NZ221570A patent/NZ221570A/en unknown
- 1987-08-26 KR KR1019870009313A patent/KR900004106B1/en not_active Expired
- 1987-08-26 CN CN87105898A patent/CN1021436C/en not_active Expired - Fee Related
- 1987-08-27 JP JP62214128A patent/JPH0637517B2/en not_active Expired - Lifetime
-
1989
- 1989-08-01 PH PH39031A patent/PH27397A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY101823A (en) | 1992-01-31 |
| PL156175B1 (en) | 1992-02-28 |
| CN1021436C (en) | 1993-06-30 |
| JPS6368598A (en) | 1988-03-28 |
| PT85581A (en) | 1987-09-01 |
| YU155987A (en) | 1989-02-28 |
| IL83657A (en) | 1992-03-29 |
| KR880002896A (en) | 1988-05-12 |
| PL267444A1 (en) | 1988-07-21 |
| EG18303A (en) | 1992-12-30 |
| CN87105898A (en) | 1988-03-09 |
| PT85581B (en) | 1990-05-31 |
| NZ221570A (en) | 1989-09-27 |
| JPH0637517B2 (en) | 1994-05-18 |
| DK444887A (en) | 1988-02-28 |
| IL83657A0 (en) | 1988-01-31 |
| PH27397A (en) | 1993-06-21 |
| KR900004106B1 (en) | 1990-06-15 |
| DK444887D0 (en) | 1987-08-26 |
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