Benzyl Bromide → HCID 86751288, compound

HRID 1379182Notes

Reaction equation

HRID 1379182 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([C@@H:9]([CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl Bromide2×HCID 24758Sodium hydrideHCID 86751289HCID 86751289, compound

Product 1

HCID 86751288HCID 86751288, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of benzyl (2S)-2-[N-(tert-butoxycarbonyl)amino]-3-(2-naphthyl)propionate (5.0 g) in dimethylformamide (50 ml) was added dropwise to a stirred mixture of 60% sodium hydride (0.6 g) and dimethylformamide (50 ml) at ice-bath temperature. After the addition was completed, the reaction mixture was stirred at the same temperature for 30 minutes. Benzyl bromide (1.76 ml) was added and then the whole mixture was stirred for 3.5 hours. Additional benzyl bromide (0.4 ml) was added and then stirred for 2.5 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed successively with 1N hydrochloric acid, aqueous sodium bicarbonate solution and brine and dried over magnesium sulfate. After evaporation of the solvent in vacuo, the residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and ethyl acetate (4:1) to give benzyl (2S)-2-[N-(tert-butoxycarbonyl)-N-benzylamino]-3-(2-naphthyl)propionate (3.53 g).

Workup

  1. additionAfter the addition
  2. stirringthe whole mixture was stirred for 3.5 hours
  3. stirringstirred for 2.5 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed successively with 1N hydrochloric acid, aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporation of the solvent in vacuo
  8. customthe residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-cb4be7e738d84c17bcf0dbd458a4954e
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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