Imiglitazar → sodium (4E)-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoate

HRID 584494Notes

Reaction equation

HRID 584494 reaction equation
C[O-].[Na+:3].[CH3:4][C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH2:16][O:17][C:18]1[CH:38]=[CH:37][C:21]([CH2:22][O:23]/[N:24]=[C:25](/[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)\[CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:20][CH:19]=1>CO>[CH3:4][C:5]1[O:9][C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:7][C:6]=1[CH2:16][O:17][C:18]1[CH:38]=[CH:37][C:21]([CH2:22][O:23]/[N:24]=[C:25](/[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)\[CH2:26][CH2:27][C:28]([O-:30])=[O:29])=[CH:20][CH:19]=1.[Na+:3]

Participants

4

Reactant 2

HCID 9890879ImiglitazarHCID 10942334Sodium Methoxide

Product 1

HCID 23671703sodium (4E)-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoateYield 46.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (108 mg) was added to a solution of E-4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutyric acid (941 mg) in methanol (5 ml), which was stirred at room temperature for 1 hour and concentrated. The remaining crystals were recrystallized from methanol-diethyl ether to obtain sodium E-4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutyrate (456 mg, yield 46%) as colorless crystals. m.p. 64-70° C.

Workup

  1. concentrationconcentrated
  2. customThe remaining crystals were recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-af7f8916321642a585504828a7746174
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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