Citric Acid → HCID 67492207, compound

HRID 1920946Notes

Reaction equation

HRID 1920946 reaction equation
[BH4-].[Li+].[CH3:3][O:4][C:5]([C:7]1[O:11][N:10]=[C:9]([O:12][CH2:13][C:14]2[C:15]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[N:16][O:17][C:18]=2[CH:19]=[O:20])[CH:8]=1)=[O:6].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:3][O:4][C:5]([C:7]1[O:11][N:10]=[C:9]([O:12][CH2:13][C:14]2[C:15]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)=[N:16][O:17][C:18]=2[CH2:19][OH:20])[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4148881Lithium borohydrideHCID 86644370HCID 86644370, compound

Product 1

HCID 67492207HCID 67492207, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Lithium borohydride (762.5 mg, 19.4 mmol) was added to a solution of 3-[3-(4-fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-isoxazole-5-carboxylic acid methyl ester (2.9 g, 8.4 mmol) in methanol (168 mL) and the resulting mixture stirred for 1 h at room temperature. Citric acid (10%, 100 mL) was then added and the resulting mixture extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica, ethyl acetate:heptane=1:4 to 1:1) afforded the title compound (1.63 g, 48%) as a white solid. MS: m/e=407.2 [M+AcO]−.

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by chromatography (silica, ethyl acetate:heptane=1:4 to 1:1)

Sources & evidence

ORD record
ord-f526df2b11314e64ae4b16f23427aad2
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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