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Acetyl chloride → methyl 2-bromo-D-phenylalaninate hydrochloride

HRID 1854540
Notes
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Reaction equation

HRID 1854540 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH2:4][C@H:5]([C:7]([OH:9])=[O:8])[NH2:6].[C:14]([Cl:17])(=O)C>CO>[ClH:17].[Br:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH2:4][C@H:5]([C:7]([O:9][CH3:14])=[O:8])[NH2:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 7023575(2R)-2-amino-3-(2-bromophenyl)propanoic acid

Product 1

HCID 117720502methyl 2-bromo-D-phenylalaninate hydrochlorideYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 2-bromo-D-phenylalanine (22.4 g, 91.8 mmol) in methanol (459 mL). Add acetyl chloride (65.3 mL, 917.7 mmol) at room temperature. Stir for 36 hours. Concentrate under reduced pressure to give the title compound (27.2 g, 92.3 mmol). MS (m/z): 258 (M+1).

Workup

  1. customat room temperature
  2. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-8063687b5ec2455dabf95f5caa4ac33f
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08962654B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes