Benzyl Bromide → HCID 66638818, compound

HRID 1094455Notes

Reaction equation

HRID 1094455 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C@H:4]([NH2:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C(#N)C>[CH3:1][O:2][C:3](=[O:14])[C@H:4]([N:13]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 15298362HCID 15298362, compound

Product 1

HCID 66638818HCID 66638818, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (R)-2-Amino-3-(2-fluoro-phenyl)-propionic acid methyl ester (4 g, 17 mmol) and benzyl bromide (4.5 mL, 38 mmol) in 200 mL of acetonitrile is added potassium carbonate. After 5 hours the reaction is heated at 50° C. for 16 hours. The reaction mixture is then cooled to room temperature and is poured into 500 mL of saturated ammonium chloride. The product is extracted into dichloromethane and the combined organic phases are dried over sodium sulfate, filtered and concentrated. Purification of the crude residue by silica gel flash column chromatography gives the title compound.

Workup

  1. temperatureThe reaction mixture is then cooled to room temperature
  2. extractionThe product is extracted into dichloromethane
  3. dry with materialthe combined organic phases are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the crude residue by silica gel flash column chromatography

Sources & evidence

ORD record
ord-715f968eaa3849d2996c5a3e92571e90
Source dataset
uspto-grants-2012_03
Patent number
US08133907B2

Reaction notes

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