Diethyl (ethoxymethylene)malonate → (S)-Diethyl (7,8-Difluoro-3-Methyl-3,4-Dihydro-2H-[1,4]Benzoxazin-4-Yl)Methylene-Malonate

HRID 8475

Reaction equation

HRID 8475 reaction equation
CC(C)([O-])C.[K+].F[C:8]1[C:18]([F:19])=[C:17]([F:20])[CH:16]=[CH:15][C:9]=1[NH:10][C@@H:11]([CH3:14])[CH2:12][OH:13].C(O[CH:24]=[C:25]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27])C>CN(C=O)C>[F:20][C:17]1[CH:16]=[CH:15][C:9]2[N:10]([CH:24]=[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[C@@H:11]([CH3:14])[CH2:12][O:13][C:8]=2[C:18]=1[F:19]

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 11089557(S)-Diethyl (7,8-Difluoro-3-Methyl-3,4-Dihydro-2H-[1,4]Benzoxazin-4-Yl)Methylene-MalonateYield 65.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To DMF (2 ml) was added potassium tertiary-butoxide (226 mg) under ice-cooling. After dropping a solution of the compound (100 mg) obtained in Example 51 and diethyl ethoxymethylenemalonate (293 mg) in DMF (0.5 ml), the resultant mixture was stirred at room temperature for 18 hours. After treating in a conventional manner, the obtained residue was subjected to silica gel column chromatography to thereby give 113 mg (65%) of the title compound. The physical constants of the obtained compounds was identical with those described in Japanese Patent No. 2,769,174.

Workup

  1. temperaturecooling
  2. additionAfter treating in a conventional manner

Sources & evidence

ORD record
ord-03f445e855fe427bb8ab9a84c995bd04
Source dataset
uspto-grants-2006_08
Patent number
US07087778B2

Linked notes

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