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

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Chemical Name:5-{5-Amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid [(3S,5S)-1-(2-amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-amide
CAS No.:642478-95-3
Molecular Formula:C₄₆H₆₅N₅O₇S₄
Molecular Weight:928.315
Hs Code.:

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

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

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

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

There total 10 articles about 5-{5-Amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid [(3S,5S)-1-(2-amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-amide 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

: 642478-95-3
5-{5-Amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid [(3S,5S)-1-(2-amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-amide

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:

: 642478-92-0
5-{4-[(S)-2-(Bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentanoic acid [(3S,5S)-1-(4-benzyloxy-5-methoxy-2-nitro-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-amide

: 642478-95-3
5-{5-Amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid [(3S,5S)-1-(2-amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-amide

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

Reference yield:

: 5454-83-1
5-bromovaleric acid methyl ester

: 642478-95-3
5-{5-Amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid [(3S,5S)-1-(2-amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-amide

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / K₂CO₃ / dimethylformamide / 24 h / 20 °C

2: 78 percent / aq. LiOH / methanol; tetrahydrofuran / 12 h / 20 °C

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

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

With lithium hydroxide; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tin(ll) chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2003.08.071