Water → HCID 59002986, compound

HRID 561125Notes

Reaction equation

HRID 561125 reaction equation
[F:1][C:2]1[C:26]([F:27])=[C:25]([F:28])[C:24](F)=[C:23](F)[C:3]=1[C:4]([C:6](=[CH:12][NH:13][C@@H:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:15]O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[H-].[Na+].[OH2:33]>C1COCC1>[F:1][C:2]1[C:3]2[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12][N:13]3[C@@H:14]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:15][O:33][C:24]([C:23]=23)=[C:25]([F:28])[C:26]=1[F:27]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 178472052HCID 178472052, compound

Product 1

HCID 59002986HCID 59002986, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl (S)-2-(2,3,4,5,6-pentafluorobenzoyl)-3-[(2-hydroxy-1-phenylethyl)amino]acrylate (2.15 g, 5.00 mmol) in THF (20 mL) was added NaH (440 mg, 11.0 mmol, 60% in oil) at 0° C. and the mixture was stirred at 0° C. for 0.5 h, at room temperature for 1 h, and then refluxed for 2 h. The mixture was treated portionwise at 0° C. with water. A precipitate formed and was collected by filtration, washed successively with EtOAc and then dried to give ethyl (S)-8,9,10-trifluoro-2,3-dihydro-7-oxo-3-phenyl-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate (465 mg, 24%) as a pale yellow solid.

Workup

  1. temperaturerefluxed for 2 h
  2. customA precipitate formed
  3. filtrationwas collected by filtration
  4. washwashed successively with EtOAc
  5. customdried

Sources & evidence

ORD record
ord-df5d36170ff94c56918d9580fd702d99
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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