Trifluoroborane-methyl sulfide → N-[3,5-dichloro-4-(4-hydroxy-3-isopropyl-5-methylphenoxy)benzoyl]glycine

HRID 860955Notes

Reaction equation

HRID 860955 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)=[C:25]([CH3:34])[CH:24]=2)=[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:24]=[C:25]([CH3:34])[C:26]([OH:32])=[C:27]([CH:29]([CH3:30])[CH3:31])[CH:28]=1)[C:14]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:36]

Participants

4

Reactant 2

HCID 11137191Trifluoroborane-methyl sulfideHCID 69384050methyl-N-[3,5-dichloro-4-(5-isopropyl-4-methoxy-3-methylphenoxy)benzoyl]glycine

Product 1

HCID 9822937N-[3,5-dichloro-4-(4-hydroxy-3-isopropyl-5-methylphenoxy)benzoyl]glycineYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride dimethyl sulfide (1.48 mL, 13.7 mmol) was added at 4° C. to a stirred solution of methyl-N-[3,5-dichloro-4-(5-isopropyl-4-methoxy-3-methylphenoxy)benzoyl]glycine (155 mg, 0.352 mmol) and dichloromethane (15 mL). The reaction mixture was stirred at room temperature for 24 hours and then treated with ice-water (30 mL), extracted with ethyl acetate and concentrated. The residue was purified on column (MPLC, silica gel, chloroform/methanol/acetic acid, gradient elution from 1/0/0 to 95/5/0.5) to give 110 mg (76%) of N-[3,5-dichloro-4-(4-hydroxy-3-isopropyl-5-methylphenoxy)benzoyl]glycine. LC-MS (ES−1): m/z 410.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationconcentrated
  3. customThe residue 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-329fb5140a894ddda3e46511e1c7eaea
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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