5-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid (8-benzyloxy-7-methoxy-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)-amide

Base Information

• Chemical Name: 5-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid (8-benzyloxy-7-methoxy-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)-amide
• CAS No.: 642479-10-5
• Molecular Formula: C₄₂H₅₃N₅O₈S₂
• Molecular Weight: 820.044

Synonyms:5-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid (8-benzyloxy-7-methoxy-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)-amide

Chemical Property of 5-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid (8-benzyloxy-7-methoxy-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)-amide

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of 5-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid (8-benzyloxy-7-methoxy-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)-amide

There total 10 articles about 5-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid (8-benzyloxy-7-methoxy-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 5-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid (8-benzyloxy-7-methoxy-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)-amide (642479-10-5)

Guidance literature:

Multi-step reaction with 7 steps

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

2: 78 percent / TEA / CH₂Cl₂ / 5 h / 0 °C

3: 68 percent / SnCl₂*2H₂O / methanol / 2 h / Heating

4: 76 percent / NaN₃ / dimethylformamide / 16 h / 60 °C

5: 72 percent / TPP; H₂O / tetrahydrofuran / 8 h / 20 °C

6: HOBT; EDCI / CH₂Cl₂; H₂O / 8 h / 20 °C

7: SnCl₂*2H₂O / methanol / 2 h / Heating

With thionyl chloride; sodium azide; TEA; water; thiamine diphosphate; 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:

5-{4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentanoic acid (8-benzyloxy-7-methoxy-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)-amide (642479-07-0) → 5-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid (8-benzyloxy-7-methoxy-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)-amide (642479-10-5)

Guidance literature:

With tin(ll) chloride; In methanol; for 2h; Heating;

DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

5-bromovaleric acid methyl ester (5454-83-1) → 5-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid (8-benzyloxy-7-methoxy-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)-amide (642479-10-5)

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 / 2 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

upstream raw materials:

5-{4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentanoic acid (8-benzyloxy-7-methoxy-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)-amide

5-bromovaleric acid methyl ester

4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid

L-4-hydroxyproline methyl ester hydrochloride

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