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HRID2172998

反应详情

EQUATION

反应方程式

HRID 2172998 的结构方程式

REACTANTS

反应物

3
结构：CC(=O)OCC(=O)Cl
HCID26297

2-Chloro-2-oxoethyl acetate

C4H5ClO3

结构：CCN(C(C)C)C(C)C
HCID81531

Diisopropylethylamine

C8H19N

结构：CCOC(=O)[C@H]1[C@@H]2[C@H](N)[C@@H](OCc3ccc(Cl)c(Cl)c3)[C@@](NC(=O)OC(C)(C)C)(C(=O)OCC)[C@H]12
HCID86695982

未命名化合物

PRODUCTS

生成物

1
结构：CCOC(=O)[C@H]1[C@@H]2[C@H](NC(=O)COC(C)=O)[C@@H](OCc3ccc(Cl)c(Cl)c3)[C@@](NC(=O)OC(C)(C)C)(C(=O)OCC)[C@H]12
HCID86695981

未命名化合物

收率 76.4%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

Add acetoxyacetyl chloride (0.116 mL, 1.08 mmol) to a solution of diethyl (1S,2R,3R,4S,5R,6S)-4-amino-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (0.47 g, 0.89 mmol) and diisoproylethylamine (0.32 mL, 1.83 mmol) in dichloromethane (9 mL) at room temperature. After 2.5 hours, wash the solution with saturated NaHCO3 (2×), brine (1×), dry over MgSO4, filter, and conc. under reduced pressure. Purify by flash chromatography eluting with a gradient of 0 to 100% ethyl acetate in hexanes over 30 min. to yield the title compound as a white solid (0.43 g, 0.68 mmol, 76%). MS (m/z): 531 (M+H-BOC).

WORKUP

后处理

  1. washwash the solution with saturated NaHCO3 (2×), brine (1×)
  2. dry with materialdry over MgSO4
  3. filtrationfilter
  4. customPurify by flash chromatography
  5. washeluting with a gradient of 0 to 100% ethyl acetate in hexanes over 30 min.