Ethyl chloroformate → HCID 56989384, compound

HRID 1940646Notes

Reaction equation

HRID 1940646 reaction equation
[C:1]([NH:4][CH2:5][CH:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][CH3:27])=[O:25])[CH2:20][CH2:19]3)=[C:14]([F:28])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2].[C:29]([O-])(O)=O.[Na+].ClC(OCC)=O>CC(C)=O.O>[C:1]([NH:4][CH2:5][CH:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:19][CH2:20][N:21]([C:24]([O:26][CH2:27][CH3:29])=[O:25])[CH2:22][CH2:23]3)=[C:14]([F:28])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 9908625HCID 9908625, compound

Product 1

HCID 56989384HCID 56989384, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

The same procedure as followed in Example 1, steps a-k, were followed. Then a solution of 100 mg (0.30 mmol) of N-((3-(4-(3-fluoro-4-(1-piperazinyl))phenyl)-2-oxo-5-oxazolidinyl)methyl)-acetamide (23) (the product from step k above) and 50 mg (0.59 mmol) of solid NaHCO3 in 2 mL acetone and 1 mL water at 0° C. was treated with 35 mg (31 μL, 0.33 mmol) of ethyl chloroformate. The solution was stirred at 0° C. for 2 hours, followed by warming to ambient temperature for 18 hours. The solution was diluted with 30 mL water and was extracted with 40 mL ethyl acetate. The organic layer was washed with 30 mL water and 30 mL saturated NaHCO3 solution. Drying (Na2SO4) and concentration in vacuo afforded a white solid. This material was subjected to radial chromatography on a 2 mm plate, eluting with 2% (v/v) methanol in chloroform. These procedures afforded 70 mg (58%) of 4-(4-(5-((acetylamino)methyl)-2-oxo-3-oxazolidinyl)-2-fluorophenyl)-1-piperazinecarboxylic acid, ethyl ester (24) as a white solid, mp=224°-226° C.

Workup

  1. temperatureby warming to ambient temperature for 18 hours
  2. extractionwas extracted with 40 mL ethyl acetate
  3. washThe organic layer was washed with 30 mL water and 30 mL saturated NaHCO3 solution
  4. customDrying
  5. concentration(Na2SO4) and concentration in vacuo
  6. customafforded a white solid
  7. washeluting with 2% (v/v) methanol in chloroform

Sources & evidence

ORD record
ord-750d4a6631e64259b303239887790430
Source dataset
uspto-grants-1997_12
Patent number
US05700799

Reaction notes

Loading…