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

HRID 545337ノート

反応式

HRID 545337 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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]

出典と根拠

ORDレコード
ord-04d500085abb4729b06bc6a641f4f90b
出典データセット
uspto-grants-2011_05
特許番号
US07935707B2

反応ノート

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