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

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Chemical Name: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
CAS No.:642479-07-0
Molecular Formula:C₄₂H₅₁N₅O₁₀S₂
Molecular Weight:850.026
Hs Code.:

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-1<i>H</i>-benzo[<i>e</i>]pyrrolo[1,2-<i>a</i>][1,4]diazepin-2-yl)-amide

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 9 articles about 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 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

: 642479-07-0
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

Guidance literature:: Multi-step reaction with 6 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

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:

: 625457-61-6
(2S)-N-{4-[(4'-carboxybutyl)oxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal

: 642479-04-7
2-amino-8-benzyloxy-7-methoxy-1,2,3,11a-tetrahydro-10H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11-dione

: 642479-07-0
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

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; water; at 20 ℃; for 8h;
DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

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

: 642479-07-0
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

Guidance literature:: Multi-step reaction with 3 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

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