Boron tribromide → N-(2,6-dichlorobenzoyl)-4-(6-methoxy-2-hydoxyphenyl)-L-phenylalanine ethyl ester

HRID 24643Notes

Reaction equation

HRID 24643 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:3]=1[C:4]([NH:6][C@H:7]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([O:21]C)=[CH:19][CH:18]=[CH:17][C:16]=2[O:23][CH3:24])=[CH:11][CH:10]=1)=[O:5].B(Br)(Br)Br>C(Cl)Cl>[CH2:28]([O:27][C:25](=[O:26])[C@H:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([O:23][CH3:24])=[CH:17][CH:18]=[CH:19][C:20]=2[OH:21])=[CH:11][CH:10]=1)[NH:6][C:4](=[O:5])[C:3]1[C:2]([Cl:1])=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:34])[CH3:29]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 131723776HCID 131723776, compound

Product 1

HCID 54105918N-(2,6-dichlorobenzoyl)-4-(6-methoxy-2-hydoxyphenyl)-L-phenylalanine ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

N-(2,6-Dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine, ethyl ester (0.16 g, prepared in a fashion similar to that of the methyl ester described in Example 8) was dissolved in anhydrous CH2Cl2 (8 mL). The solution was cooled to −78° C. and BBr3 (0.56 mL, 1 M solution in CH2Cl2) was added. The mixture was allowed to warm to 0° C., and stirred at that temperature for 2 h. The mixture was subsequently warmed to room temperature and quenched with satd. NaHCO3 (5 mL). The mixture was stirred for 1 h, and diluted with CH2Cl2. The organic phase was dried (MgSO4) and concentrated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexanes 1:2) to give 40 mg of N-(2,6-dichlorobenzoyl)-4-(2-hydroxy-6-methoxyphenyl)-L-phenylalanine ethyl ester ESMS: m/z 488 (MH+).

Workup

  1. temperatureto warm to 0° C.
  2. temperatureThe mixture was subsequently warmed to room temperature
  3. customquenched with satd
  4. stirringThe mixture was stirred for 1 h
  5. additiondiluted with CH2Cl2
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexanes 1:2)

Sources & evidence

ORD record
ord-5064c68e27ac4a6793ee45a6e654b8d1
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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