Citric Acid → HCID 136376011, compound

HRID 2276223Notes

Reaction equation

HRID 2276223 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-methylphenyl)-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 anti-isomers.

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-9c902d09ade545f292c3aedd7e48f9f5
Source dataset
uspto-grants-2015_09
Patent number
USRE045670E1

Reaction notes

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