Tetra-n-butylammonium tribromide → N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3-bromophenyl)-L-phenylalanine methyl ester

HRID 24690

Reaction equation

HRID 24690 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=2[O:31][CH3:32])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14].[Br-:34].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24]([O:31][CH3:32])=[CH:25][CH:26]=[C:27]([Br:34])[C:28]=2[O:29][CH3:30])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14]

Participants

4

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromide2×HCID 54326841N-(2,6-Dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester

Product 1

HCID 54021971N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3-bromophenyl)-L-phenylalanine methyl esterYield 164.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2,6-Dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester (1.01 g) was dissolved in CH2Cl2 (40 mL) under N2 and tetrabutylammonium tribromide (1.21 g) was added and the mixture was stirred at room temperature overnight. More tetrabutylammonium tribromide (0.55 g) was added and the mixture was stirred for 1 day. The mixture was then washed with water (25 mL) and the organic layer was dried (MgSO4), filtered and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: hexane and AcOEt) to give N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3-bromophenyl)-L-phenylalanine methyl ester (1.17 g).

Workup

  1. stirringthe mixture was stirred for 1 day
  2. washThe mixture was then washed with water (25 mL)
  3. dry with materialthe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash column chromatography (silica gel; eluent: hexane and AcOEt)

Sources & evidence

ORD record
ord-fb60bdad71084c1daabe0104a210fd3f
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Linked notes

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