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

HRID 1854541Notes

Reaction equation

HRID 1854541 reaction equation
[C:1]([Cl:4])(=O)C.[Br:5][C:6]1[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=1[CH2:8][C@H:9]([C:11]([OH:13])=[O:12])[NH2:10]>CO>[ClH:4].[Br:5][C:6]1[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=1[CH2:8][C@H:9]([C:11]([O:13][CH3:1])=[O:12])[NH2:10]

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 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
17.5 °C

Procedure

Add acetyl chloride (562.79 g, 7.17 mol) to methanol (10.00 L) at 0° C. in an appropriate vessel. Heat the mixture to 17.5° C. and stir. After 30 minutes, add 2-bromo-D-phenylalanine (500.00 g, 2.05 moles) and heat to reflux. After 4 hours, cool to 20° C. and remove the solvent under reduced pressure to give the title compound (589 g, 1.96 mol) as an off-white solid. MS (m/z): 258 (M-Cl (79Br)), 260 (M-Cl (81Br)).

Workup

  1. temperatureheat to reflux
  2. waitAfter 4 hours
  3. temperaturecool to 20° C.
  4. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-81884e92c1654979820814e45f033481
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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