tert-butyl (R)-4-[(S)-2-(azido-2-methoxycarbonylethyl)(tolyl-4'-sulfonyl)aminocarbonyl]-2,2-dimethylthiazolidine-3-carboxylate

Base Information

Chemical Name:tert-butyl (R)-4-[(S)-2-(azido-2-methoxycarbonylethyl)(tolyl-4'-sulfonyl)aminocarbonyl]-2,2-dimethylthiazolidine-3-carboxylate
CAS No.:1154035-27-4
Molecular Formula:C₂₂H₃₁N₅O₇S₂
Molecular Weight:541.649
Hs Code.:

Synonyms:tert-butyl (R)-4-[(S)-2-(azido-2-methoxycarbonylethyl)(tolyl-4'-sulfonyl)aminocarbonyl]-2,2-dimethylthiazolidine-3-carboxylate

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Chemical Property of tert-butyl (R)-4-[(S)-2-(azido-2-methoxycarbonylethyl)(tolyl-4'-sulfonyl)aminocarbonyl]-2,2-dimethylthiazolidine-3-carboxylate

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Technology Process of tert-butyl (R)-4-[(S)-2-(azido-2-methoxycarbonylethyl)(tolyl-4'-sulfonyl)aminocarbonyl]-2,2-dimethylthiazolidine-3-carboxylate

There total 4 articles about tert-butyl (R)-4-[(S)-2-(azido-2-methoxycarbonylethyl)(tolyl-4'-sulfonyl)aminocarbonyl]-2,2-dimethylthiazolidine-3-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: 90.0%

: 5317-15-7
(4R)-3-(tert-butoxycarbonyl)-2,2-dimethylthiazolidine-4-carboxylic acid

: 1154035-19-4
(S)-2-azido-3-(4’-tolyl-sulfonylamino)-propionic acid methyl ester

: 1154035-27-4
tert-butyl (R)-4-[(S)-2-(azido-2-methoxycarbonylethyl)(tolyl-4'-sulfonyl)aminocarbonyl]-2,2-dimethylthiazolidine-3-carboxylate

Guidance literature:: (4R)-3-(tert-butoxycarbonyl)-2,2-dimethylthiazolidine-4-carboxylic acid; With caesium carbonate; HATU; In dichloromethane; at 0 ℃; for 0.25h; Inert atmosphere;

(S)-2-azido-3-(4’-tolyl-sulfonylamino)-propionic acid methyl ester; With caesium carbonate; In dichloromethane; at 0 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201300160

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 1154035-27-4
tert-butyl (R)-4-[(S)-2-(azido-2-methoxycarbonylethyl)(tolyl-4'-sulfonyl)aminocarbonyl]-2,2-dimethylthiazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydrogencarbonate; sodium hydroxide / water; 1,4-dioxane / 2.5 h / 0 - 20 °C / pH 9 / Inert atmosphere

2.1: thionyl chloride / 6 h / 0 - 20 °C / Inert atmosphere

3.1: triflic azide; triethylamine; copper(II) sulfate / methanol; water; dichloromethane / 20 °C / Inert atmosphere

4.1: caesium carbonate; HATU / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

4.2: 0 °C / Inert atmosphere

With thionyl chloride; triflic azide; sodium hydrogencarbonate; caesium carbonate; copper(II) sulfate; triethylamine; HATU; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; water;
DOI:10.1002/ejoc.201300160

Reference yield:

: 72071-27-3
(S)-2-tert-butoxycarbonylamino-3-(tolyl-4'-sulfonylamino)-propionic acid

: 1154035-27-4
tert-butyl (R)-4-[(S)-2-(azido-2-methoxycarbonylethyl)(tolyl-4'-sulfonyl)aminocarbonyl]-2,2-dimethylthiazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: thionyl chloride / 6 h / 0 - 20 °C / Inert atmosphere

2.1: triflic azide; N-ethyl-N,N-diisopropylamine; copper(II) sulfate / dichloromethane; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

3.1: caesium carbonate; HATU / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

With thionyl chloride; triflic azide; caesium carbonate; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201300160