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

HRID 1854542Notes

Reaction equation

HRID 1854542 reaction equation
Cl.[Br:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH2:5][C@H:6]([C:8]([O:10][CH3:11])=[O:9])[NH2:7].C(=O)(O)[O-].[Na+].Cl[C:22]([O:24][CH3:25])=[O:23]>ClCCl.O>[Br:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH2:5][C@H:6]([C:8]([O:10][CH3:11])=[O:9])[NH:7][C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 3

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

Product 1

HCID 117720331Methyl 2-bromo-N-(methoxycarbonyl)-D-phenylalaninateYield 99.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Dissolve methyl 2-bromo-D-phenylalaninate hydrochloride (27.2 g, 92.3 mmol) in dichloromethane (923 mL) and water (185 mL). Add sodium bicarbonate (31.0 g, 369.4 mmol) and methyl chloroformate (7.86 mL, 101.6 mmol) at room temperature. Stir the mixture 2.5 hours. Dilute with water and extract with dichloromethane. Dry the dichloromethane extracts over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue by silica gel chromatography eluting with ethyl acetate:hexanes (10-75% gradient) to give the title compound (29.1 g, 92.1 mmol). MS (m/z): 316 (M+1).

Workup

  1. customat room temperature
  2. extractionextract with dichloromethane
  3. dry with materialDry the dichloromethane
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by silica gel chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-ea68e76439b446e3b46232b65c975f31
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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