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HRID2117702

反应详情

EQUATION

反应方程式

HRID 2117702 的结构方程式

REACTANTS

反应物

3
结构：CCN(C(C)C)C(C)C
HCID81531

Diisopropylethylamine

C8H19N

结构：CC(=O)Nc1cccc(S(=O)(=O)Cl)c1
HCID3157455

3-acetamidobenzene-1-sulfonyl chloride

C8H8ClNO3S

结构：CC(C)(CCC#N)CNC[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]1CO[C@H]2OCC[C@H]21
HCID59815752

未命名化合物

PRODUCTS

生成物

1
结构：CC(=O)Nc1cccc(S(=O)(=O)N(C[C@@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CO[C@H]3OCC[C@H]32)CC(C)(C)CCC#N)c1
HCID480328

未命名化合物

收率 59.1%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

[(1S,2R)-1-Benzyl-3-(4-cyano-2,2-dimethylbutylamino)-2-hydroxy-propyl]-carbamic acid (3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-yl ester (0.020 g, 0.05 mmol) was dissolved in CH2Cl2 and treated with diisopropylethylamine (0.025 ml, 0.13 mmol) and 3-acetamidobenzenesulfonyl chloride (0.012 g, 0.05 mmol) at ambient temperature under argon with stirring. After 15 h the reaction mixture was concentrated in vacuo, taken up in EtOAc, washed with sat. aq. NaHCO3, and brine. The organic phase was dried over MgSO4, filtered and solvent removed in vacuo. Purification by preparative thin layer chromatography (3% MeOH in CH2Cl2) gave 0.019 g of a white solid. MS (ES): 643 (M+1).

WORKUP

后处理

  1. concentrationAfter 15 h the reaction mixture was concentrated in vacuo
  2. washwashed with sat. aq. NaHCO3, and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customsolvent removed in vacuo
  6. customPurification by preparative thin layer chromatography (3% MeOH in CH2Cl2)