Citric Acid → HCID 136376011, compound

HRID 131926Notes

Reaction equation

HRID 131926 reaction equation
[C:1]([O-:4])(O)=[O:2].[Na+].[CH:6]1([C:11]([C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=2[NH:20][C:21]([NH:23][C:24]2[S:25][C:26]([CH:29]=O)=[CH:27][N:28]=2)=[O:22])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1.Cl.[NH2:32][OH:33].[C:34](O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH:6]1([C:11]([C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=2[NH:20][C:21](=[O:22])[NH:23][C:24]2[S:25][C:26]([CH:29]=[N:32][O:33][CH2:34][C:1]([OH:4])=[O:2])=[CH:27][N:28]=2)=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 59733046HCID 59733046, compound

Product 1

HCID 136376011HCID 136376011, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 2M aq NaHCO3 (5 mL) and 1-(2-cyclopentanecarbonyl-4-methyl-phenyl)-3-(5-formyl-thiazol-2-yl)-urea (72 mg, 0.2 mmol) in THF (5 mL) was added hydroxylamine hydrochloride (200 mg) at room temperature with stirring. The resulting mixture was heated at 60° C. for 12 h. The reaction mixture was cooled, acidified to pH 6.5 (citric acid) and extracted with ethyl acetate. The organic layer was washed (brine), dried (Na2SO4) and concentrated to obtain {2-[3-(2-cyclopentanecarbonyl-4-methyl-phenyl)-ureido]-thiazol-5-ylmethyleneaminooxy}-acetic acid (56 mg, 76%) as a mixture of syn and antiisomers.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed (brine)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-98913472549a426fbeecb6c71f9fecea
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Reaction notes

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