Water → Methyl 2-bromo-N-(methoxycarbonyl)-D-phenylalaninate

HRID 1854543Notes

Reaction equation

HRID 1854543 reaction equation
O.C(=O)([O-])O.[Na+].Cl.[Br:8][C:9]1[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=1[CH2:11][C@H:12]([C:14]([O:16][CH3:17])=[O:15])[NH2:13].Cl[C:23]([O:25][CH3:26])=[O:24]>ClCCl>[Br:8][C:9]1[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=1[CH2:11][C@H:12]([C:14]([O:16][CH3:17])=[O:15])[NH:13][C:23]([O:25][CH3:26])=[O:24]

Participants

6

Reactant 4

HCID 962Water2×HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 117720502methyl 2-bromo-D-phenylalaninate hydrochloride

Product 1

HCID 117720331Methyl 2-bromo-N-(methoxycarbonyl)-D-phenylalaninateYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Add water (2.94 L) and sodium hydrogen carbonate (648.25 g, 7.64 mol) to methyl 2-bromo-D-phenylalaninate hydrochloride (580 g, 1.91 mol) in dichloromethane (9.86 L) at 10° C. in an appropriate vessel. After 5 minutes add methyl chloroformate (198.53 g, 2.10 mol) and stir the mixture at 20° C. After 3 hours add water (2.5 L) and separate the layers. Extract the aqueous with dichloromethane, dry the combined organic extracts over sodium sulfate and concentrate under reduced pressure to give the title compound (556 g, 1.74 mol). MS (m/z): 315.8 (M+1 (79Br)), 317.8 (M+1 (81Br)).

Workup

  1. customseparate the layers
  2. extractionExtract the aqueous with dichloromethane
  3. dry with materialdry the combined organic extracts over sodium sulfate
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-8b9147aa1f8b406eb30c5f562c6139f3
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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