Acetoxyacetyl chloride → HCID 69365792, compound

HRID 723790Notes

Reaction equation

HRID 723790 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([N:15]3[CH2:19][C@H:18]([CH2:20][N:21]4[CH:25]=[CH:24][N:23]=[N:22]4)[O:17][C:16]3=[O:26])=[CH:10][C:9]=2[F:27])=[CH:4][CH2:3]1.C(=O)(O)[O-].[Na+].[C:33]([O:36][CH2:37][C:38](Cl)=[O:39])(=[O:35])[CH3:34]>CC(C)=O.O>[C:33]([O:36][CH2:37][C:38]([N:2]1[CH2:7][CH2:6][C:5]([C:8]2[C:9]([F:27])=[CH:10][C:11]([N:15]3[CH2:19][C@H:18]([CH2:20][N:21]4[CH:25]=[CH:24][N:23]=[N:22]4)[O:17][C:16]3=[O:26])=[CH:12][C:13]=2[F:14])=[CH:4][CH2:3]1)=[O:39])(=[O:35])[CH3:34]

Participants

6

Reactant 3

HCID 26297Acetoxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 69364600HCID 69364600, compound

Product 1

HCID 69365792HCID 69365792, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of (5R)-3-(4-(1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one hydrochloride (650 mg, 1.64 mM) in acetone (20 ml) and water (10 ml), was treated with sodium bicarbonate (1.38 g, 16.4 mM) and the mixture cooled to 0–4°. Acetoxyacetyl chloride (448 mg, 3.28 mM) was added dropwise and the reaction mixture stirred at 0–4° for 20 minutes before allowing to warm to ambient temperature. After dilution with water the mixture was extracted well with ethyl acetate. The organic phase was separated, dried (sodium sulfate), solvent evaporated, and the residue triturated with diethyl ether to give the desired product (702 mg).

Workup

  1. temperaturethe mixture cooled to 0–4°
  2. extractionAfter dilution with water the mixture was extracted well with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried (sodium sulfate), solvent
  5. customevaporated
  6. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-aa85adb0c4804dae94be6b3e8b24d7c0
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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