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

Base Information

Chemical Name:methyl (2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxylate
CAS No.:625123-46-8
Molecular Formula:C₂₇H₃₆N₂O₈Si
Molecular Weight:544.677
Hs Code.:

Synonyms:methyl (2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxylate

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Chemical Property of methyl (2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxylate

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Technology Process of methyl (2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxylate

There total 4 articles about methyl (2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-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: 92.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 382137-65-7
methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate

: 625123-46-8
methyl (2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxylate

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/S0960-894X(03)00718-2

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 625123-46-8
methyl (2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

2: 80 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

With 1H-imidazole; thionyl chloride; water; In dichloromethane; benzene;
DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

: 60547-92-4
4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid

: 625123-46-8
methyl (2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: thionyl chloride; DMF / benzene / 6 h

2: 75 percent / triethylamine / tetrahydrofuran; H₂O / 1 h / 20 °C

3: 90 percent / imidazole / CH₂Cl₂ / 12 h / 20 °C

With 1H-imidazole; thionyl chloride; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; water; benzene;
DOI:10.1016/j.bmc.2004.06.013