Benzyl Bromide → HCID 10647114, compound

HRID 742024Notes

Reaction equation

HRID 742024 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:26])[C@@H:9]([CH2:22][CH:23]([CH3:25])[CH3:24])[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12])([CH3:6])([CH3:5])[CH3:4].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([S:11]([N:10]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:9]([CH2:22][CH:23]([CH3:24])[CH3:25])[C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:26])(=[O:13])=[O:12])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10808269N-[4-methoxybenzenesulfonyl]-(D)-leucine t-butyl ester

Product 1

HCID 10647114HCID 10647114, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (0.68 g, 14.1 mmol) in dimethylformamide (60.0 mL), is added N-[4-methoxybenzenesulfonyl]-(D)-leucine t-butyl ester (5.02 g, 14.06 mmol) in dimethylformamide (10.0 mL). After stirring at room temperature for 20 minutes, benzyl bromide (1.67 mL, 14.06 mmol) is added, and the reaction is stirred overnight at room temperature. The reaction is then partitioned between ethyl acetate and acidic water (pH=5), the organic layer is dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (10% ethyl acetate/hexane) to give t-butyl 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-4-methylpentanoate.

Workup

  1. stirringthe reaction is stirred overnight at room temperature
  2. customThe reaction is then partitioned between ethyl acetate and acidic water (pH=5)
  3. dry with materialthe organic layer is dried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe product is purified by silica gel chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-56c97bcc23194e65b07c11fc2aaa593c
Source dataset
uspto-grants-1996_09
Patent number
US05552419

Reaction notes

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