Dichloromethane → HCID 10387174, compound

HRID 860963Notes

Reaction equation

HRID 860963 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]([F: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]([F: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 69388350HCID 69388350, compound

Product 1

HCID 10387174HCID 10387174, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Boron trifluoride dimethyl sulfide (2.0 mL) was added at room temperature to a stirred solution of methyl-N-[3,5-dichloro-4-(3-fluoro-5-isopropyl-4-methoxyphenoxy)benzoyl]glycine (50 mg, 0.11 mmol) and dichloromethane (8 mL). The reaction mixture was stirred at room temperature for 24 hours, poured out in water and extracted with ethyl acetate. The combined organic phases were washed with water, concentrated and the resulting residue purified on column (HPLC, ACE-C8, acetonitrile/0.05% formic acid in water, gradient elution from 5/95 to 60/40) to give 5 mg (20%) of N-[3,5-dichloro-4-(3-fluoro-4-hydroxy-5-isopropylphenoxy)benzoyl]glycine. LC-MS (ES−1): m/z 414.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with water
  3. concentrationconcentrated
  4. customthe resulting residue purified on column (HPLC, ACE-C8, acetonitrile/0.05% formic acid in water, gradient elution from 5/95 to 60/40)

Sources & evidence

ORD record
ord-f2003dc4611e4d269787ee08d5f6ba81
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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