Acetyl chloride → 2-Acetamido-2-[(acetyloxy)methyl]-4-(4-acetylphenyl)butyl acetate

HRID 853813노트

반응식

HRID 853813 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)([CH3:7])=[O:6].[C:9]([O:12][CH2:13][C:14]([NH:28][C:29](=[O:31])[CH3:30])([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:15][O:16][C:17](=[O:19])[CH3:18])(=[O:11])[CH3:10]>ClCCCl>[C:17]([O:16][CH2:15][C:14]([NH:28][C:29](=[O:31])[CH3:30])([CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:5](=[O:6])[CH3:7])=[CH:26][CH:27]=1)[CH2:13][O:12][C:9](=[O:11])[CH3:10])(=[O:19])[CH3:18]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10543752ACETAMIDE, N-[1,1-BIS[(ACETYLOXY)METHYL]-3-PHENYLPROPYL]-

생성물 1

HCID 534715242-Acetamido-2-[(acetyloxy)methyl]-4-(4-acetylphenyl)butyl acetate

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

실험 절차

To a suspension of AlCl3 (16 mmol) in DCE (20 mL) is added AcCl (8 mmol) in one portion. After stirring at room temperature for 30 minutes, to the solution is added acetic acid 2-acetoxymethyl-2-acetylamino-4-phenyl-butyl ester (2 mmol) in DCE (5 mL). After an additional 30 minutes, the mixture is poured into ice-cold 1 N NaOH and is extracted with DCM. The organic phase is washed with 1 N HCl, brine and dried over Na2SO4. After concentrating, the crude material is purified by column chromatography using EtOAc/hexane (2/1) to give acetic acid 2-acetoxymethyl-2-acetylamino-4-(4-acetyl-phenyl)-butyl ester as a white solid. MS: (ES+): 364.2 (M+1)+.

후처리

  1. waitAfter an additional 30 minutes
  2. extractionis extracted with DCM
  3. washThe organic phase is washed with 1 N HCl, brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentrating
  6. customthe crude material is purified by column chromatography

출처 및 근거

ORD 기록
ord-e05edd0fb14b4902b1885996ed0c55a6
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07256206B2

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