Diethyl (ethoxymethylene)malonate → Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate

HRID 985691Notes

Reaction equation

HRID 985691 reaction equation
[F:1][C:2]1[C:12]([F:13])=[C:11]([F:14])[CH:10]=[CH:9][C:3]=1[NH:4][C@@H:5]([CH3:8])[CH2:6][OH:7].C(O[CH:18]=[C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])C>>[F:1][C:2]1[C:12]([F:13])=[C:11]([F:14])[CH:10]=[CH:9][C:3]=1[N:4]([CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C@@H:5]([CH3:8])[CH2:6][OH:7]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanol

Product 1

HCID 11485652Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonateYield 78%

Conditions

Temperature
100 °C

Procedure

To the compound (103 mg) obtained in Example 51 was added diethyl ethoxymethylenemalonate (127 mg). Then the obtained mixture was stirred for 1 hour while heating to 100° C. under atmospheric pressure. Further, it was stirred at the same temperature for 1.5 hour under reduced pressure and then under atmospheric pressure for additional 16 hours. By analyzing reversed phase HPLC with the use of the compound of Example 63 as a specimen, the obtained product corresponded to 142 mg (78%) of the title compound.

Workup

  1. stirringFurther, it was stirred at the same temperature for 1.5 hour under reduced pressure
  2. waitunder atmospheric pressure for additional 16 hours

Sources & evidence

ORD record
ord-41c098ba0b71477188006845fd9f21cb
Source dataset
uspto-grants-2005_03
Patent number
US06872823B1

Reaction notes

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