Boron tribromide → {3-[2-tert-Butylsulfanylmethyl-4-(2,2-dimethyl-propionylamino)-phenoxy]-4-hydroxy-phenyl}-acetic acid

HRID 888538Notes

Reaction equation

HRID 888538 reaction equation
[C:1]([S:5][CH2:6][C:7]1[CH:25]=[C:24]([NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH:23]=[CH:22][C:8]=1[O:9][C:10]1[CH:11]=[C:12]([CH2:18][C:19]([OH:21])=[O:20])[CH:13]=[CH:14][C:15]=1[O:16]C)([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[C:1]([S:5][CH2:6][C:7]1[CH:25]=[C:24]([NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH:23]=[CH:22][C:8]=1[O:9][C:10]1[CH:11]=[C:12]([CH2:18][C:19]([OH:21])=[O:20])[CH:13]=[CH:14][C:15]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 44600763Am-461

Product 1

HCID 44600128{3-[2-tert-Butylsulfanylmethyl-4-(2,2-dimethyl-propionylamino)-phenoxy]-4-hydroxy-phenyl}-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{3-[2-tert-Butylsulfanylmethyl-4-(2,2-dimethyl-propionylamino)-phenoxy]-4-methoxy-phenyl}-acetic acid (0.953 g, 2.07 mmol) in CH2Cl2 was cooled to 0° C. Boron tribromide (1M in CH2Cl2; 6.21 mL, 6.21 mmol) was added, and the reaction was stirred at room temperature for 2 hours. The reaction was quenched, and after aqueous work-up, the crude material was purified by preparative HPLC to give the title compound.

Workup

  1. customThe reaction was quenched
  2. customafter aqueous work-up, the crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-d0645a7b3167416aa5ab8c7fd8e0104f
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

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