Benzyl Bromide → HCID 54194702, compound

HRID 1375035Notes

Reaction equation

HRID 1375035 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([NH:16][C@@H:17]([C:28]([OH:30])=[O:29])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH3:27])[CH:20]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[CH2:1]([O:30][C:28](=[O:29])[C@H:17]([NH:16][C:14]([O:13][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:15])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH3:27])[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 46737392HCID 46737392, compound

Product 1

HCID 54194702HCID 54194702, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (2.34 ml, 19.8 ml) was added to a solution of N-tert-butyloxycarbonyl-4-hydroxy-3-methoxy-D-phenylalanine (3.44 g) and N,N-diisopropylethylamine (3.85 ml) in N,N-dimethylformamide (20 ml). After being stirred at room temperature for 6 hours, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of hexane and ethyl acetate (4:1) to give (2R)-2-(tert-butyloxycarbonylamino)-3-(4-hydroxy-3-methoxyphenyl)propionic acid benzyl ester (2.98 g) as colorless powders.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additiona mixture of hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-c13c62b90c68457ea1b953390fe3e88c
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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