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HRID458358

反应详情

EQUATION

反应方程式

HRID 458358 的结构方程式

REACTANTS

反应物

2
结构：C[Si](C)(C)N=C=O
HCID70696

Trimethylsilyl isocyanate

C4H9NOSi

结构：c1ccc(COC[C@@H]2C[C@@H](SC(c3ccccc3)(c3ccccc3)c3ccccc3)CN2)cc1
HCID69427603

未命名化合物

PRODUCTS

生成物

1
结构：NC(=O)N1C[C@H](SC(c2ccccc2)(c2ccccc2)c2ccccc2)C[C@H]1COCc1ccccc1
HCID69431348

未命名化合物

收率 47%

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 400 mg (0.86 mmol) (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine in 15 ml CH2Cl2 with 0.3 ml (2.2 mmol) trimethylsilylisocyanate and a catalytic amount of DMAP was stirred over night. The reaction was extracted with aqueous 10% KHSO4/EtOAc (3×) and the organic phase was dried over Na2SO4. Crystallization (CH2Cl2/MeOH/Et2O) gave 205 mg (47%) (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid amide, MS: 509 (MH+).

WORKUP

后处理

  1. extractionThe reaction was extracted with aqueous 10% KHSO4/EtOAc (3×)
  2. dry with materialthe organic phase was dried over Na2SO4
  3. customCrystallization (CH2Cl2/MeOH/Et2O)