Benzyl Bromide → HCID 66625251, compound

HRID 416536Notes

Reaction equation

HRID 416536 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH:13]([OH:18])[CH2:14][C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.C([O-])(O)=O.[Na+]>[CH2:19]([O:16][C:15](=[O:17])[CH2:14][CH:13]([OH:18])[CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 2

HCID 7498Benzyl BromideHCID 111185764-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoic acid

Product 1

HCID 66625251HCID 66625251, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 5.0 g (19.7 mmol) 4-benzyloxycarbonylamino-3-hydroxy-butyric acid and 6.36 g (1 equiv.) tetra-n-butyl ammonium bromide in 70 ml dichloromethane and 50 ml of an aqueous saturated NaHCO3-solution were added 2.35 ml (1 equiv.) benzyl bromide. The resulting mixture was stirred vigorously for 72 h at room temperature. The organic layer was separated, washed three times with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate) gave pure 4-benzyloxycarbonylamino-3-hydroxy-butyric acid benzyl ester as colorless oil.

Workup

  1. customThe organic layer was separated
  2. washwashed three times with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography on silica gel (eluent: heptane/ethyl acetate)

Sources & evidence

ORD record
ord-a2028ad28b3744ebbfdf06bf8c5c2196
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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