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HRID20445

反应详情

EQUATION

反应方程式

HRID 20445 的结构方程式

REACTANTS

反应物

3
结构：CC(C)CBr
HCID6555

1-Bromo-2-methylpropane

C4H9Br

结构：O=C([O-])[O-].[Cs+].[Cs+]
HCID10796

Cesium carbonate

CCs2O3

结构：CC(=O)N[C@@H](Cc1cc(O)cc(F)c1)[C@H](O)[C@H]1CO[C@@H](OCC(C)(C)C)[C@H](C)N1C(=O)OC(C)(C)C
HCID68560537

未命名化合物

PRODUCTS

生成物

1
结构：CC(=O)N[C@@H](Cc1cc(F)cc(OCC(C)C)c1)[C@H](O)[C@H]1CO[C@@H](OCC(C)(C)C)[C@H](C)N1C(=O)OC(C)(C)C
HCID68561946

未命名化合物

收率 55%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

结构：CCOC(C)=O
溶剂HCID8857

Ethyl acetate

C4H8O2

CONDITIONS

反应条件

温度
60 °C

PROCEDURE

实验过程

Add 1-bromo-2-methyl-propane (0.05 g, 0.35 mmol) to (2R,3S,5R)-5-[(1S,2S)-2-acetylamino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxy-propyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester (0.12 g, 0.23 mmol) and cesium carbonate (0.15 g, 0.46 mmol) in N,N-dimethylformamide (3 mL) under nitrogen and heat in a 60° C. oil bath for 2.5 hours. Cool to room temperature and dilute with ethyl acetate. Wash (0.1N citric acid, 10% potassium carbonate, saturated aqueous sodium chloride), dry (magnesium sulfate), filter and concentrate. Purify on 12 g silica gel column eluting with 100:0 to 40:60 hexanes:ethyl acetate to give 0.072 g (54.5%) of the title compound as a white foam.

WORKUP

后处理

  1. temperatureCool to room temperature
  2. washWash (0.1N citric acid, 10% potassium carbonate, saturated aqueous sodium chloride)
  3. dry with materialdry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify on 12 g silica gel column
  7. washeluting with 100:0 to 40:60 hexanes