Acetyl chloride → HCID 69430374, compound

HRID 1375919Notes

Reaction equation

HRID 1375919 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)([CH3:7])=[O:6].[C:9]([O:12][CH2:13][C:14]([NH:34][C:35](=[O:37])[CH3:36])([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[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:34][C:35](=[O:37])[CH3:36])([CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:5](=[O:6])[CH3:7])=[CH:30][CH:29]=2)=[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 58787872HCID 58787872, compound

Product 1

HCID 69430374HCID 69430374, compound

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 min, to the solution is added acetic acid 2-acetoxymethyl-2-acetylamino-4-biphenyl-4-yl-butyl ester (2 mmol) in DCE (5 mL). After an additional 30 min, 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 the desired product as a white solid. MS: (ES+): 439.2 (M+1)+.

Workup

  1. waitAfter an additional 30 min
  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-3622e039358844bba3bf5577a676e4b0
Source dataset
uspto-grants-2007_01
Patent number
US07169817B2

Reaction notes

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