Dichloromethane → N-[3,5-dichloro-4-(3-chloro-4-hydroxy-5-isopropylphenoxy)benzoyl]glycine

HRID 860959Notes

Reaction equation

HRID 860959 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]([Cl:34])[CH:24]=2)=[C:17]([Cl:35])[CH:16]=1)[CH2:10][C:11]([OH:13])=[O:12].ClCCl>O>[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])=[C:25]([Cl:34])[CH:24]=1)[C:14]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:36]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11137191Trifluoroborane-methyl sulfideHCID 69384319methyl-N-[3,5-dichloro-4-(3-chloro-5-isopropyl-4-methoxyphenoxy)benzoyl]glycine

Product 1

HCID 10342790N-[3,5-dichloro-4-(3-chloro-4-hydroxy-5-isopropylphenoxy)benzoyl]glycine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Boron trifluoride dimethyl sulfide (1.0 mL) was added at room temperature to a stirred solution of methyl-N-[3,5-dichloro-4-(3-chloro-5-isopropyl-4-methoxyphenoxy)benzoyl]glycine (90 mg) and dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 24 hours, poured out in water and extracted with ethyl acetate (3×30 mL). The combined organic phases were washed with water (4×20 mL), concentrated and the resulting residue purified on column (silica gel, chloroform/methanol/acetic acid 94:6:0.65). This gave 53 mg (63%) of N-[3,5-dichloro-4-(3-chloro-4-hydroxy-5-isopropylphenoxy)benzoyl]glycine. LC-MS (ES+1): m/z 434.

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. washThe combined organic phases were washed with water (4×20 mL)
  3. concentrationconcentrated
  4. customthe resulting residue purified on column (silica gel, chloroform/methanol/acetic acid 94:6:0.65)

Sources & evidence

ORD record
ord-b407689baaa2499fb15074ff97864076
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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