Benzyl Bromide → HCID 54383845, compound

HRID 2210482Notes

Reaction equation

HRID 2210482 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1)[NH:5][C:6](=[O:14])[C:7](=[N:12][OH:13])[CH2:8][CH:9]([CH3:11])[CH3:10].[H-].[Na+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Cl-].[NH4+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1)[NH:5][C:6](=[O:14])[C:7](=[N:12][O:13][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:8][CH:9]([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86749041HCID 86749041, compound

Product 1

HCID 54383845HCID 54383845, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7.50 g of N-(2-hydroxyimino-4-methylpentanoyl)-(3,4,5-trimethoxy)phenylalanine methyl ester in dried dimethylformamide (150 ml) was added 0.9 g of sodium hydride (60%), and the mixture was stirred at room temperature for 1 hour. Then 2.75 ml of benzyl bromide was added to the reaction mixture and further stirred at room temperature for 2 hours. The reaction mixture was transferred to an aqueous solution saturated with ammonium chloride under an ice-cooling condition, then was extracted with ethyl acetate. The organic layer was washed with an aqueous solution saturated with sodium chloride in three times, and was dried with magnesium sulfate, and the solvent was removed by distillation, the resulting residue was purified by means of a silica gel column chromatography (eluent: ethyl acetate:n-hexane=l:3) to obtain 8.35 g of N-(2-benzyloxyimino-4-methylpentanoyl)-(3,4,5-trimethoxy)phenylalanine methyl ester.

Workup

  1. stirringfurther stirred at room temperature for 2 hours
  2. temperaturecooling condition
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous solution saturated with sodium chloride in three times
  5. dry with materialwas dried with magnesium sulfate
  6. customthe solvent was removed by distillation
  7. customthe resulting residue was purified by means of a silica gel column chromatography (eluent: ethyl acetate:n-hexane=l:3)

Sources & evidence

ORD record
ord-9480ac3a60aa4040a35c367f5b48c8a9
Source dataset
uspto-grants-1995_10
Patent number
US05459142

Reaction notes

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