Benzoic acid (2S,4S)-4-azido-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (2S,4S)-4-azido-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester
CAS No.:22324-35-2
Molecular Formula:C₁₉H₂₀N₄O₄S
Molecular Weight:400.458
Hs Code.:

Synonyms:Benzoic acid (2S,4S)-4-azido-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

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Chemical Property of Benzoic acid (2S,4S)-4-azido-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

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Technology Process of Benzoic acid (2S,4S)-4-azido-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

There total 5 articles about Benzoic acid (2S,4S)-4-azido-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl 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: 78.0%

: 22324-34-1
(2S,4R)-N-Tosyl-4-tosyloxy-O-benzoylprolinol

: 22324-35-2
Benzoic acid (2S,4S)-4-azido-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; 1.) 70 deg C, 18 h, 2.) room temperature, 48 h;
DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

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

: 22324-35-2
Benzoic acid (2S,4S)-4-azido-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / Et₃N, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

2: LiBH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 1 h

3: 91 percent / Et₃N, DMAP / CH₂Cl₂

4: 78 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 18 h, 2.) room temperature, 48 h

With dmap; lithium borohydride; sodium azide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

: 118329-82-1
(2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

: 22324-35-2
Benzoic acid (2S,4S)-4-azido-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / Et₃N, DMAP / CH₂Cl₂

2: 78 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 18 h, 2.) room temperature, 48 h

With dmap; sodium azide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00821-7