5-[(2S,4S)-4-Mercapto-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester

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Chemical Name:5-[(2S,4S)-4-Mercapto-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester
CAS No.:262297-27-8
Molecular Formula:C₁₈H₂₁N₃O₇S
Molecular Weight:423.447
Hs Code.:

Synonyms:5-[(2S,4S)-4-Mercapto-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester

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Chemical Property of 5-[(2S,4S)-4-Mercapto-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester

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Technology Process of 5-[(2S,4S)-4-Mercapto-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester

There total 5 articles about 5-[(2S,4S)-4-Mercapto-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester 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:

: 262297-26-7
5-[(2S,4S)-4-Acetylsulfanyl-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester

: 262297-27-8
5-[(2S,4S)-4-Mercapto-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester

Guidance literature:: With sodium hydroxide; In methanol; at 20 ℃; for 0.5h;
DOI:10.1016/S0960-894X(99)00646-0

Reference yield:

: 262297-18-7
(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-vinyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

: 262297-27-8
5-[(2S,4S)-4-Mercapto-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 47 percent / Et₃N / dioxane; CH₂Cl₂ / 20 °C

2: 85 percent / TBAF / tetrahydrofuran / 0.5 h

3: 94 percent / Et₃N / CH₂Cl₂

4: 73 percent / acetonitrile / 5 h / Heating

5: 1 N NaOH / methanol / 0.5 h / 20 °C

With sodium hydroxide; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetonitrile; 1: Cycloaddition / 2: desilylation / 3: mesylation / 4: Substitution / 5: Deacetylation;
DOI:10.1016/S0960-894X(99)00646-0

Reference yield:

: 5-[(2S,4R)-4-Hydroxy-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester

: 262297-27-8
5-[(2S,4S)-4-Mercapto-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / Et₃N / CH₂Cl₂

2: 73 percent / acetonitrile / 5 h / Heating

3: 1 N NaOH / methanol / 0.5 h / 20 °C

With sodium hydroxide; triethylamine; In methanol; dichloromethane; acetonitrile; 1: mesylation / 2: Substitution / 3: Deacetylation;
DOI:10.1016/S0960-894X(99)00646-0