HCID 54320048, compound → HCID 68698537, compound

HRID 2247032Notes

Reaction equation

HRID 2247032 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][CH:3]1[CH3:26].[F:27][C:28]([Mg]Br)([F:30])[F:29]>O1CCCC1>[F:27][C:28]([F:30])([F:29])[C:2]1([OH:1])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][CH:3]1[CH3:26]

Participants

4

Reactant 2

HCID 54320048HCID 54320048, compoundHCID 178506352HCID 178506352, compound

Product 1

HCID 68698537HCID 68698537, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By reacting (S)-N-{3-[4-(4-oxo-3-methyl-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (2.40 mmol) and trifluoromethyl magnesium bromide (2.6 mmol) in tetrahydrofuran (20 ml) followed by silica gel chromatographic separation of diastereomer the compound was obtained in 78% yield. M.P. 144-146° C. and MS (M+1)=434 (MH+, 100%) for M.F.=C19H23F4N3O4.

Workup

  1. customfollowed by silica gel chromatographic separation of diastereomer the compound
  2. customwas obtained in 78% yield

Sources & evidence

ORD record
ord-241c3dc862144140a186be72fff21ad6
Source dataset
uspto-grants-2010_03
Patent number
US07687627B2

Reaction notes

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