tert-Butyl bromoacetate → N-(3,4-dichlorophenyl)alanine Tert-butyloxycarbonylmethyl Ester

HRID 411428

Reaction equation

HRID 411428 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C@H:10]([C:12]([OH:14])=[O:13])[CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>>[C:20]([O:19][C:17]([CH2:16][O:13][C:12](=[O:14])[C@H:10]([CH3:11])[NH:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 5491659N-(3,4-dichlorophenyl)alanine

Product 1

HCID 54406316N-(3,4-dichlorophenyl)alanine Tert-butyloxycarbonylmethyl Ester

Procedure

Following General Procedure AE above and using N-(3,4-dichlorophenyl)alanine (from Example AB above) and tert-butyl bromoacetate (Aldrich), the title compound was prepared as a solid. The reaction was monitored by silica gel tlc (Rf=0.57 in 25% EtOAc/hexanes). Purification was by recrystallization from ethanol.

Workup

  1. customPurification
  2. customwas by recrystallization from ethanol

Sources & evidence

ORD record
ord-ec2cd4f582e846b8bdbace523e827e05
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Linked notes

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