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HRID20372

反应详情

EQUATION

反应方程式

HRID 20372 的结构方程式

REACTANTS

反应物

3
结构：CC(=O)OC(C)=O
HCID7918

Acetic anhydride

C4H6O3

结构：CCN(CC)CC
HCID8471

Triethylamine

C6H15N

结构：CC(C)(C)OC(=O)N1C[C@H](CCC2CCCCC2)OC[C@@H]1[C@@H](O)[C@@H](N)Cc1ccccc1
HCID68561811

未命名化合物

PRODUCTS

生成物

1
结构：CC(=O)N[C@@H](Cc1ccccc1)[C@H](O)[C@H]1CO[C@@H](CCC2CCCCC2)CN1C(=O)OC(C)(C)C
HCID68561017

未命名化合物

收率 54.8%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

Dissolve 5-(R)-(2-(S)-amino-1-(S)-hydroxy-3-phenylpropyl)-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester (140 mg, 0.31 mmol) in dry tetrahydrofuran (3 mL). Add triethylamine (0.05 mL, 0.35 mmol) followed by acetic anhydride (0.03 mL, 0.35 mmol) and stir at room temperature for 1 hour. Dilute with dichloromethane, wash with 0.1 N hydrochloric acid/saturated aqueous sodium chloride (30 mL), dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 40:60 to 60:40 ethyl acetate:dichloromethane) acetate/dichloromethane to give the title compound (83 mg, 54%).

WORKUP

后处理

  1. washwash with 0.1 N hydrochloric acid/saturated aqueous sodium chloride (30 mL)
  2. dry with materialdry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify (silica gel chromatography, eluting with 40:60 to 60:40 ethyl acetate:dichloromethane) acetate/dichloromethane