3-(1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-2-carbonyl)-5-ethyl-5-methyl-2-oxo-2λ⁴-[1,2,3]oxathiazolidine-4-carboxylic acid benzyl ester

Base Information

• Chemical Name: 3-(1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-2-carbonyl)-5-ethyl-5-methyl-2-oxo-2λ⁴-[1,2,3]oxathiazolidine-4-carboxylic acid benzyl ester
• CAS No.: 233675-30-4
• Molecular Formula: C₂₃H₃₀N₂O₇S
• Molecular Weight: 478.566

Synonyms:3-(1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-2-carbonyl)-5-ethyl-5-methyl-2-oxo-2λ⁴-[1,2,3]oxathiazolidine-4-carboxylic acid benzyl ester

Chemical Property of 3-(1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-2-carbonyl)-5-ethyl-5-methyl-2-oxo-2λ⁴-[1,2,3]oxathiazolidine-4-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of 3-(1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-2-carbonyl)-5-ethyl-5-methyl-2-oxo-2λ⁴-[1,2,3]oxathiazolidine-4-carboxylic acid benzyl ester

There total 3 articles about 3-(1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-2-carbonyl)-5-ethyl-5-methyl-2-oxo-2λ⁴-[1,2,3]oxathiazolidine-4-carboxylic acid benzyl 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: 75.0%

(S)-2-((1S,2S)-1-Benzyloxycarbonyl-2-hydroxy-2-methyl-butylcarbamoyl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (233675-29-1) → 3-(1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-2-carbonyl)-5-ethyl-5-methyl-2-oxo-2λ4-[1,2,3]oxathiazolidine-4-carboxylic acid benzyl ester (233675-30-4)

Guidance literature:

With thionyl chloride; In dichloromethane;

DOI:10.1021/ja991037q

Reference yield:

(S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester (51154-06-4) → 3-(1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-2-carbonyl)-5-ethyl-5-methyl-2-oxo-2λ4-[1,2,3]oxathiazolidine-4-carboxylic acid benzyl ester (233675-30-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / Et₃N, BOP

2: 75 percent / SOCl₂ / CH₂Cl₂

With thionyl chloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In dichloromethane;

DOI:10.1021/ja991037q

Reference yield:

benzyl ester β-hydroxyleucine → 3-(1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-2-carbonyl)-5-ethyl-5-methyl-2-oxo-2λ4-[1,2,3]oxathiazolidine-4-carboxylic acid benzyl ester (233675-30-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / Et₃N, BOP

2: 75 percent / SOCl₂ / CH₂Cl₂

With thionyl chloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In dichloromethane;

DOI:10.1021/ja991037q

upstream raw materials:

(S)-2-((1S,2S)-1-Benzyloxycarbonyl-2-hydroxy-2-methyl-butylcarbamoyl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

(S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester

Downstream raw materials:

(S)-2-((E)-1-Benzyloxycarbonyl-2-methyl-but-1-enylcarbamoyl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

2-(1-benzyloxycarbonyl-2-methyl-but-1-enyl)-tert-butoxycarbonyl-aminocarbonyl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

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