(S)-2,2,2-Trichloro-1-phenylethyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoate → 3-Methyl 5-((S)-2,2,2-trichloro-1-phenylethyl) 4-(2,3-dichlorophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate

HRID 1789022Notes

Reaction equation

HRID 1789022 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]=[C:10]([C:25](=O)[CH3:26])[C:11]([O:13][C@@H:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]([Cl:18])([Cl:17])[Cl:16])=[O:12].[NH2:28][C:29]([CH2:35][F:36])=[CH:30][C:31]([O:33][CH3:34])=[O:32]>C(O)(C)(C)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:10]([C:11]([O:13][C@@H:14]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:15]([Cl:18])([Cl:17])[Cl:16])=[O:12])=[C:25]([CH3:26])[NH:28][C:29]([CH2:35][F:36])=[C:30]1[C:31]([O:33][CH3:34])=[O:32]

Participants

4

Reactant 2

HCID 53903953(S)-2,2,2-Trichloro-1-phenylethyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoateHCID 73668923Methyl 3-amino-4-fluoro-2-butenoate

Product 1

HCID 867417213-Methyl 5-((S)-2,2,2-trichloro-1-phenylethyl) 4-(2,3-dichlorophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

(S)-2,2,2-Trichloro-1-phenylethyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoate (10.8 g, 23 mmoles) and methyl 3-amino-4-fluoro-2-butenoate (3.7 g, 28 mmoles) were heated at 55° in dry tert-butanol (50 ml) for 68 hours. The solvent was removed and the residue purified and separated into single diastereomers by HPLC eluting with methylene chloride/petroleum ether (60°-80° ) mixtures.

Workup

  1. customThe solvent was removed
  2. customthe residue purified
  3. customseparated into single diastereomers by HPLC
  4. washeluting with methylene chloride/petroleum ether (60°-80° ) mixtures

Sources & evidence

ORD record
ord-85f0f7b4499d44979dd6f292fd589555
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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