Citric Acid → HCID 178477457, compound

HRID 2194490Notes

Reaction equation

HRID 2194490 reaction equation
[CH2:1]([S:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[CH:8]=[C:7]([C:15]([O:17]C2CCCC(=O)C=2)=O)[C:6]1=[O:25])[CH3:2].C(N(CC)CC)C.C[C:34]([CH3:38])([OH:37])[C:35]#N.[C:39](O)(=O)[CH2:40][C:41](CC(O)=O)(C(O)=O)[OH:42]>ClCCl>[CH2:1]([S:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[CH:8]=[C:7]([C:15]([C:35]2[C:41](=[O:42])[CH2:40][CH2:39][CH2:38][C:34]=2[OH:37])=[O:17])[C:6]1=[O:25])[CH3:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 67010060HCID 67010060, compound

Product 1

HCID 178477457HCID 178477457, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.97 g (8.3 mmol) of 3-oxo-1-cyclohexenyl 1-(ethylthiomethyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in dichloromethane (80 mL). 1.40 mL (10.0 mmol) of triethylamine and 0.77 g (9.1 mmol) of acetone cyanohydrin were added to the above solution, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was poured into an aqueous solution of citric acid, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried, and concentrated. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:4), and thus 0.77 g of the title compound was obtained as pale orange-colored crystals (yield: 26%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record
ord-b3d8d4a30fb5438ca68e7b83a1cdf44d
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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