Hydrochloric Acid → HCID 66961011, compound

HRID 1667648Notes

Reaction equation

HRID 1667648 reaction equation
[CH2:1]([N:8]([C:15]1[CH:16]=[C:17]([C:33]2[CH:38]=[CH:37][C:36]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:35][CH:34]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1)[C:9](=[O:14])[C:10]([O:12]C)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+].Cl>O1CCCC1>[CH2:1]([N:8]([C:15]1[CH:16]=[C:17]([C:33]2[CH:34]=[CH:35][C:36]([O:39][C:40]([F:41])([F:42])[F:43])=[CH:37][CH:38]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1)[C:9](=[O:14])[C:10]([OH:12])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59821001HCID 59821001, compound

Product 1

HCID 66961011HCID 66961011, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl N-benzyl-N-{4-[4-(tert-butyl)benzyloxy]-4′-(trifluoromethoxy)biphenyl-3-yl}oxamate (115 mg, 0.194 mmol), methanol (11.0 ml), 2N aqueous sodium hydroxide (0.2 ml) and tetrahydrofuran (11.0 ml) was stirred at room temperature for 1 hour. The reaction mixture was adjusted to pH 5-6 by addition of 2N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (ethyl acetate methanol=4:1) to give the title compound (75 mg, 67%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by column chromatography on silica gel (ethyl acetate methanol=4:1)

Sources & evidence

ORD record
ord-a2740d3805b3423ba981554633a0cbfa
Source dataset
uspto-grants-2011_10
Patent number
US08044236B2

Reaction notes

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