N-[(3S,5S)-1-(2-Amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-butyramide

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Chemical Name:N-[(3S,5S)-1-(2-Amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-butyramide
CAS No.:642478-94-2
Molecular Formula:C₄₅H₆₃N₅O₇S₄
Molecular Weight:914.289
Hs Code.:

N-[(3S,5S)-1-(2-Amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-butyramide

Synonyms:N-[(3S,5S)-1-(2-Amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-butyramide

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Chemical Property of N-[(3S,5S)-1-(2-Amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-butyramide

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Technology Process of N-[(3S,5S)-1-(2-Amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-butyramide

There total 11 articles about N-[(3S,5S)-1-(2-Amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-butyramide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 642478-94-2
N-[(3S,5S)-1-(2-Amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-butyramide

Guidance literature:: Multi-step reaction with 9 steps

1: 75 percent / SOCl₂; H₂O / benzene / 2 h / 20 °C

2: 80 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

3: 70 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4: 62 percent / TMSCl / CH₂Cl₂ / 8 h / 20 °C

5: 78 percent / TEA / CH₂Cl₂ / 5 h / 0 °C

6: 76 percent / NaN₃ / dimethylformamide / 16 h / 60 °C

7: 72 percent / TPP; aq. NH₃ / tetrahydrofuran / 8 h / 20 °C

8: HOBt; EDCI / CH₂Cl₂; H₂O / 8 h / 20 °C

9: SnCl₂*2H₂O / methanol / 6 h / Heating

With 1H-imidazole; ammonium hydroxide; chloro-trimethyl-silane; thionyl chloride; sodium azide; TEA; water; thiamine diphosphate; diisobutylaluminium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tin(ll) chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

: 642478-91-9
N-[(3S,5S)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-butyramide

: 642478-94-2
N-[(3S,5S)-1-(2-Amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-butyramide

Guidance literature:: With tin(ll) chloride; In methanol; for 6h; Heating;
DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

: 60547-92-4
4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid

: 642478-94-2
N-[(3S,5S)-1-(2-Amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-butyramide

Guidance literature:: Multi-step reaction with 9 steps

1: 75 percent / SOCl₂; H₂O / benzene / 2 h / 20 °C

2: 80 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

3: 70 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4: 62 percent / TMSCl / CH₂Cl₂ / 8 h / 20 °C

5: 78 percent / TEA / CH₂Cl₂ / 5 h / 0 °C

6: 76 percent / NaN₃ / dimethylformamide / 16 h / 60 °C

7: 72 percent / TPP; aq. NH₃ / tetrahydrofuran / 8 h / 20 °C

8: HOBt; EDCI / CH₂Cl₂; H₂O / 8 h / 20 °C

9: SnCl₂*2H₂O / methanol / 6 h / Heating

With 1H-imidazole; ammonium hydroxide; chloro-trimethyl-silane; thionyl chloride; sodium azide; TEA; water; thiamine diphosphate; diisobutylaluminium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tin(ll) chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.bmcl.2003.08.071