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HRID2204980

反应详情

EQUATION

反应方程式

HRID 2204980 的结构方程式

REACTANTS

反应物

3
结构：c1ccncc1
HCID1049

Pyridine

C5H5N

结构：CS(=O)(=O)Cl
HCID31297

Methanesulfonyl chloride

CH3ClO2S

结构：CC(C)(C)OC(=O)[C@H](CSC[C@@H](O)CO)NC(=O)OCc1ccccc1
HCID67402221

未命名化合物

PRODUCTS

生成物

1
结构：CC(C)(C)OC(=O)[C@H](CSC[C@H](COS(C)(=O)=O)OS(C)(=O)=O)NC(=O)OCc1ccccc1
HCID86678279

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CN(C)c1ccncc1
催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

A solution of (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((S)-2,3-dihydroxypropylthio)propanoate (1 eq) was stirred in dry DCM (0.1M) in an ice bath (0° C.) under an atmosphere of N2. Pyridine (8.0 eq) was then carefully added at 0° C. Methanesulfonyl chloride (4.0 eq) and DMAP (0.1 eq) were added with the reaction slowly warming to room temperature, then stirred overnight. The crude reaction mixture was then loaded directly onto a silica column and purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient of 100% Hex, 0-20% EtOAc/Hex, 20-50% EtOAc/Hex, 100% EtOAc to afford the title compound as an oil.

WORKUP

后处理

  1. customThe crude reaction mixture
  2. custompurified by flash chromatography on a COMBIFLASH® system (ISCO)