methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-[(methylsulfonyl)oxy]pyrrolidine-2-carboxylate

Base Information

• Chemical Name: methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-[(methylsulfonyl)oxy]pyrrolidine-2-carboxylate
• CAS No.: 642479-01-4
• Molecular Formula: C₂₂H₂₄N₂O₁₀S
• Molecular Weight: 508.506

Synonyms:methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-[(methylsulfonyl)oxy]pyrrolidine-2-carboxylate

Chemical Property of methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-[(methylsulfonyl)oxy]pyrrolidine-2-carboxylate

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Technology Process of methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-[(methylsulfonyl)oxy]pyrrolidine-2-carboxylate

There total 2 articles about methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-[(methylsulfonyl)oxy]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: 88.0%

methanesulfonyl chloride (124-63-0) + methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate (382137-65-7) → methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-[(methylsulfonyl)oxy]pyrrolidine-2-carboxylate (642479-01-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2008.04.006

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-[(methylsulfonyl)oxy]pyrrolidine-2-carboxylate (642479-01-4)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With thionyl chloride; TEA; water; In dichloromethane; benzene;

DOI:10.1016/j.bmcl.2003.08.071

Reference yield: 83.0%

methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-[(methylsulfonyl)oxy]pyrrolidine-2-carboxylate (642479-01-4) → (2S,4R)-methyl1-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-(methylsulfonyloxy)pyrrolidine-2-carboxylate (1238824-23-1)

Guidance literature:

With boron trifluoride diethyl etherate; ethanethiol; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tet.2010.05.003

upstream raw materials:

methanesulfonyl chloride

methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

methanesulfonic 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 ester

C₂₁H₂₁N₅O₇

(2S,4R)-methyl1-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-(methylsulfonyloxy)pyrrolidine-2-carboxylate

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