HCID 69849151, compound → HCID 22713823, compound

HRID 352188Notes

Reaction equation

HRID 352188 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:28])[C:22]=3[C:21]3=[N:29][O:30][C:31]([CH3:32])=[C:20]3[C:19]2=[O:33])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C.O>[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:27]3[C:22](=[C:23]([Cl:28])[CH:24]=[CH:25][CH:26]=3)[C:21]([NH2:29])=[C:20]([C:31](=[O:30])[CH3:32])[C:19]2=[O:33])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 69849151HCID 69849151, compound

Product 1

HCID 22713823HCID 22713823, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of [3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester (0.5 g, 1.04 mmol) and Mo(CO)6 (3.0 g, 0.01 mmol) in Acetonitrile (50 mL) and water (5 mL) was heated to 60° C. and stirred overnight. The reaction was concentrated to a solid, diluted in CH2Cl2 and filtered through Celite to remove the black insoluble material. The filtrate was concentrated to a solid and purified using silica gel column chromatography. The product was eluted with 10% EtOAc in CH2Cl2. The solvent was removed to afford 0.520 g (quantitative) of product as a light brown oil. MS (ES+) m/z 482.0 (M+H)+,(ES−) m/z 479.9 (M−H)−, 540.0 (M+CH3COO−)−.

Workup

  1. concentrationThe reaction was concentrated to a solid
  2. additiondiluted in CH2Cl2
  3. filtrationfiltered through Celite
  4. customto remove the black insoluble material
  5. concentrationThe filtrate was concentrated to a solid
  6. custompurified
  7. washThe product was eluted with 10% EtOAc in CH2Cl2
  8. customThe solvent was removed
  9. customto afford 0.520 g (quantitative) of product as a light brown oil

Sources & evidence

ORD record
ord-da86e73ddcd4464da853ecaadb5e13d9
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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