Methylamine → 4-(3-Fluorophenylsulfanyl)-2-(4-fluoro-2-trifluoromethylbenzoylamino)-3-hydroxy-N-methylbutyramide

HRID 506483Notes

Reaction equation

HRID 506483 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][CH:10]([OH:30])[CH:11]([NH:16][C:17](=[O:29])[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[C:25]([F:28])([F:27])[F:26])[C:12](OC)=[O:13])[CH:5]=[CH:6][CH:7]=1.[CH3:31][NH2:32]>CO>[F:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][CH:10]([OH:30])[CH:11]([NH:16][C:17](=[O:29])[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[C:25]([F:28])([F:27])[F:26])[C:12]([NH:32][CH3:31])=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59432160Methyl 4-(3-fluorophenylsulfanyl)-2-(4-fluoro-2-trifluoromethylbenzoylamino)-3-hydroxybutyrate

Product 1

HCID 594321514-(3-Fluorophenylsulfanyl)-2-(4-fluoro-2-trifluoromethylbenzoylamino)-3-hydroxy-N-methylbutyramide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

760 mg (about 1.5 mmol) of crude product from step 1.5 were dissolved in methanol. With gentle cooling, gaseous methylamine was then introduced for 30 min. The mixture was stirred at RT for 15 h. The solvents were then removed, the residue was stirred with MTBE and the precipitate was filtered off with suction. This gave 416 mg (62% of theory over 2 steps) of the title compound (4:1 diastereomer mixture) as a colorless solid of m.p. 172° C.

Workup

  1. customThe solvents were then removed
  2. stirringthe residue was stirred with MTBE
  3. filtrationthe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-4945d27d81cf4ed29ed2135f6cf26f19
Source dataset
uspto-grants-2010_08
Patent number
US07786046B2

Reaction notes

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