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

HRID 8484

Reaction equation

HRID 8484 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:18]=[CH:17][C:11]2[NH:12][C@@H:13]([CH3:16])[CH2:14][O:15][C:10]=2[C:9]=1[F:19].C(O[CH:23]=[C:24]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])C>CN(C=O)C>[F:7][C:8]1[CH:18]=[CH:17][C:11]2[N:12]([CH:23]=[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[C@@H:13]([CH3:16])[CH2:14][O:15][C:10]=2[C:9]=1[F:19]

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11041424(3S)-3-Methyl-7,8-difluoro-2,3-dihydro-4H-1,4-benzoxazineHCID 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 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To DMF (2.5 ml) was added potassium tertiary-butoxide (75 mg) under ice-cooling. After dropping a solution of the compound (100 mg) obtained in Example 78 and diethyl ethoxymethylenemalonate (233 mg) in DMF (0.5 ml), the resultant mixture was stirred for 2 hours. After treating in a conventional manner, the obtained residue was subjected to silica gel column chromatography to thereby give 153 mg (88%) of the title compound as an oily product. 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-4eb0b563d26541c38317838c6ee3f3f4
Source dataset
uspto-grants-2006_08
Patent number
US07087778B2

Linked notes

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