methyl (2S)-N-{4-[(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-pyrrolidine-2-carboxaldehyde diethyl thioacetal-4-(carboxamidomethylidene)-N-propyl]oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxylate

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Chemical Name:methyl (2S)-N-{4-[(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-pyrrolidine-2-carboxaldehyde diethyl thioacetal-4-(carboxamidomethylidene)-N-propyl]oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxylate
CAS No.:757190-10-6
Molecular Formula:C₄₃H₅₁N₅O₁₃S₂
Molecular Weight:910.036
Hs Code.:

methyl (2S)-N-{4-[(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-pyrrolidine-2-carboxaldehyde diethyl thioacetal-4-(carboxamidomethylidene)-N-propyl]oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxylate

Synonyms:methyl (2S)-N-{4-[(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-pyrrolidine-2-carboxaldehyde diethyl thioacetal-4-(carboxamidomethylidene)-N-propyl]oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxylate

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Chemical Property of methyl (2S)-N-{4-[(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-pyrrolidine-2-carboxaldehyde diethyl thioacetal-4-(carboxamidomethylidene)-N-propyl]oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxylate

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Technology Process of methyl (2S)-N-{4-[(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-pyrrolidine-2-carboxaldehyde diethyl thioacetal-4-(carboxamidomethylidene)-N-propyl]oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxylate

There total 9 articles about methyl (2S)-N-{4-[(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-pyrrolidine-2-carboxaldehyde diethyl thioacetal-4-(carboxamidomethylidene)-N-propyl]oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxylate 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: 67.0%

: 757190-15-1
(2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(carboxymethylidene)-pyrrolidine-2-carboxaldehyde diethyl thioacetal

: methyl (2S)-N-[4-(2-aminopropoxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxylate

: 757190-10-6
methyl (2S)-N-{4-[(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-pyrrolidine-2-carboxaldehyde diethyl thioacetal-4-(carboxamidomethylidene)-N-propyl]oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxylate

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; water; at 20 ℃;
DOI:10.1016/j.bmc.2004.06.013

Reference yield:

: 64154-78-5
4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride

: 757190-10-6
methyl (2S)-N-{4-[(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-pyrrolidine-2-carboxaldehyde diethyl thioacetal-4-(carboxamidomethylidene)-N-propyl]oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 75 percent / triethylamine / tetrahydrofuran; H₂O / 1 h / 20 °C

2: 90 percent / imidazole / CH₂Cl₂ / 12 h / 20 °C

3: 65 percent / diisobutyl aluminium hydride / hexane; CH₂Cl₂ / 0.75 h / -78 °C

4: 72 percent / trimethylsilyl chloride / CHCl₃ / 18.5 h

5: 78 percent / TPAP; NMO; molecular sieves 4 Angstroem / acetonitrile; CH₂Cl₂ / 2.5 h / 20 °C

6: 80 percent / sodium hydride / tetrahydrofuran / 2 h / 0 °C

7: 83 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O; methanol / 2 h / 20 °C

8: 67 percent / EDCI; HOBt / CH₂Cl₂; H₂O / 20 °C

With 1H-imidazole; lithium hydroxide; chloro-trimethyl-silane; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; acetonitrile;
DOI:10.1016/j.bmc.2004.06.013

Reference yield:

: 175409-49-1
methyl-(2S)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxylate

: 757190-10-6
methyl (2S)-N-{4-[(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-pyrrolidine-2-carboxaldehyde diethyl thioacetal-4-(carboxamidomethylidene)-N-propyl]oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / K₂CO₃ / dimethylformamide / 20 °C

2: trifluoroacetic acid / CH₂Cl₂ / 0 °C

3: 67 percent / EDCI; HOBt / CH₂Cl₂; H₂O / 20 °C

With potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2004.06.013