Acetic Anhydride → 2-[Cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-butyric acid ethyl ester

HRID 545337노트

반응식

HRID 545337 반응식
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]([CH:20]1[CH2:22][CH2:21]1)[C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)[CH3:2].[C:24](OC(=O)C)(=[O:26])[CH3:25]>C1COCC1.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:23])[CH:5]([N:6]([CH:20]1[CH2:22][CH2:21]1)[C:7](=[O:19])[C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]([F:16])([F:17])[F:18])=[CH:12][CH:13]=1)[C:24](=[O:26])[CH3:25])[CH3:2]

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 67133328[Cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester

생성물 1

HCID 671333462-[Cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-butyric acid ethyl ester수율 13.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 6.6 ml (1 M in THF, 7 mmol) of lithium hexamethyldisilylazide cooled to −78° C. under Ar was added, drop wise, a solution of 2.0 g (6 mmol) of [cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester in 10 ml of THF. The mixture was stirred for 1 h before 0.7 g of acetic anhydride was added and the mixture was allowed to reach room temperature. After 2 h the reaction was diluted with EtOAc, washed with saturated ammonium chloride solution, the organic phase dried with sodium sulfate and concentrated. Purification by flash column chromatography [n-heptane/EtOAc 1:9 to 3:7] afforded 0.3 g (13%) of the title compound as a colorless oil. MS: 374.2 (MH+).

후처리

  1. additionwas added
  2. additionwas added
  3. customto reach room temperature
  4. washwashed with saturated ammonium chloride solution
  5. dry with materialthe organic phase dried with sodium sulfate
  6. concentrationconcentrated
  7. customPurification by flash column chromatography [n-heptane/EtOAc 1:9 to 3:7]

출처 및 근거

ORD 기록
ord-04d500085abb4729b06bc6a641f4f90b
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935707B2

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