Triethylamine → HCID 24886341, compound

HRID 750925Notes

Reaction equation

HRID 750925 reaction equation
[C:1]([CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:20][C@H:19]([CH2:21][NH2:22])[O:18][C:17]3=[O:23])=[CH:12][C:11]=2[F:24])[CH2:6][CH2:5]1)#[N:2].C(Cl)(=O)C(Cl)=O.[F:31][CH:32]([F:36])[C:33](O)=[O:34].C(N(CC)CC)C>ClCCl>[C:1]([CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:20][C@H:19]([CH2:21][NH:22][C:33](=[O:34])[CH:32]([F:36])[F:31])[O:18][C:17]3=[O:23])=[CH:12][C:11]=2[F:24])[CH2:6][CH2:5]1)#[N:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9788Difluoroacetic acidHCID 65578Oxalyl chlorideHCID 24885852HCID 24885852, compound

Product 1

HCID 24886341HCID 24886341, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of (S)-N-{3-[4-(4-cyanomethylidene-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-amine (0.5 g, 1.45 mmol), oxalyl chloride (0.150 ml, 1.74 mmol), difluoroacetic acid (0.1 ml, 1.74 mmol) and triethylamine (0.242 ml, 1.74 mmol) in dichloromethane (20 ml) was stirred for 1 hour at room temperature. The reaction mixture was extracted with the dichloromethane water mixture. The combined organic layer was dried and removal of the solvent afforded a residue which was chromatographed over silica gel to give title compound in 48% yield.

Workup

  1. extractionThe reaction mixture was extracted with the dichloromethane water mixture
  2. customThe combined organic layer was dried
  3. customremoval of the solvent
  4. customafforded a residue which
  5. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-7319737019d447ee85bdbc952dc2eebc
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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