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

HRID 853813Notes

Reaction equation

HRID 853813 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-e05edd0fb14b4902b1885996ed0c55a6
Source dataset
uspto-grants-2007_08
Patent number
US07256206B2

Reaction notes

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