Hydrochloric Acid → HCID 10005368, compound

HRID 981281Notes

Reaction equation

HRID 981281 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]2[C:34](F)=[CH:33][C:18]([C:19]([C:21](=[CH:27][NH:28][CH:29]([CH3:32])[CH2:30][OH:31])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:20])=[C:17](F)[C:16]=2[F:37])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C(OCC)(=O)C.Cl>CN(C)C=O.O>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]2[C:16]([F:37])=[CH:17][C:18]3[C:19](=[O:20])[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][N:28]4[CH:29]([CH3:32])[CH2:30][O:31][C:34]=2[C:33]=34)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 178472009HCID 178472009, compound

Product 1

HCID 10005368HCID 10005368, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 25 ml of N,N-dimethylformamide was dissolved 3.07 g of ethyl 2-[4-(1-benzyloxycarbonylaminocyclopropyl)-2,3,5-trifluorobenzoyl]-3-(2-hydroxy-1-methylethylamino)acrylate. To the resulting solution was added 519 mg of 60% sodium hydride with ice-cooling. The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was added to a mixture of 50 ml of ethyl acetate and 50 ml of water. The resulting mixture was adjusted to pH 1 with 2N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant: toluene/ethyl acetate=1/1) to obtain 760 mg (yield: 26.9%) of ethyl 10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate.

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue obtained
  7. customwas purified by a column chromatography (eluant: toluene/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-f5fcfcdcbe2441afba9b9c9f713f12b4
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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