Trifluoroborane-methyl sulfide → N-[3,5-dichloro-4-(2-bromo-4-hydroxy-5-isopropylphenoxy)benzoyl]glycine

HRID 860958Notes

Reaction equation

HRID 860958 reaction equation
CSC.B(F)(F)F.C[N:9]([C:14](=[O:36])[C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([O:22][C:23]2[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[C:26]([O:32]C)=[CH:25][C:24]=2[Br:34])=[C:17]([Cl:35])[CH:16]=1)[CH2:10][C:11]([OH:13])=[O:12]>ClCCl>[Cl:21][C:19]1[CH:20]=[C:15]([CH:16]=[C:17]([Cl:35])[C:18]=1[O:22][C:23]1[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[C:26]([OH:32])=[CH:25][C:24]=1[Br:34])[C:14]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:36]

Participants

4

Reactant 2

HCID 11137191Trifluoroborane-methyl sulfideHCID 69384859methyl-N-[3,5-dichloro-4-(2-bromo-4-methoxy-5-isopropylphenoxy)benzoyl]glycine

Product 1

HCID 10027993N-[3,5-dichloro-4-(2-bromo-4-hydroxy-5-isopropylphenoxy)benzoyl]glycineYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride dimethyl sulfide (10 μL, 80 μmol) was added at room temperature to a stirred solution of methyl-N-[3,5-dichloro-4-(2-bromo-4-methoxy-5-isopropylphenoxy)benzoyl]glycine (1.0 mg, 2.0 μmol) and dichloromethane (0.50 mL). The reaction mixture was stirred at room temperature for 8 hours and then treated with ice-water, extracted with ethyl acetate and washed with water. The organic phase was dried over sodium sulphate and concentrated to give a light yellow solid. The solid was purified on column (MPLC, silica gel, chloroform/methanol/acetic acid, gradient elution from 1/0/0 to 95/5/0.5) to give 0.90 mg (94%) of N-[3,5-dichloro-4-(2-bromo-4-hydroxy-5-isopropylphenoxy)benzoyl]glycine. LC-MS (ES−1): m/z 476.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated
  5. customto give a light yellow solid
  6. customThe solid was purified on column (MPLC, silica gel, chloroform/methanol/acetic acid, gradient elution from 1/0/0 to 95/5/0.5)

Sources & evidence

ORD record
ord-83c5f8f9df0f407991abbe39700853e7
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

Loading…