Pyridine → 3-Carbamoylisoxazol-5-ylmethyl 4-nitrophenyl carbonate

HRID 1943594Notes

Reaction equation

HRID 1943594 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].C[NH:15][C:16]([C:18]1[CH:22]=[C:21]([CH2:23][OH:24])[O:20][N:19]=1)=[O:17].N1C=CC=CC=1>ClCCl>[C:2](=[O:3])([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[O:24][CH2:23][C:21]1[O:20][N:19]=[C:18]([C:16](=[O:17])[NH2:15])[CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 110948685-(Hydroxymethyl)-N-methylisoxazole-3-carboxamide

Product 1

HCID 666608603-Carbamoylisoxazol-5-ylmethyl 4-nitrophenyl carbonateYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.84 g (14.07 mmoles) of 4-nitrophenyl chloroformate are added in small portions to a solution of 2.0 g (14.07 mmoles) of 3-methylcarbamoyl-isoxazol-5-yl-methanol (commercial), 1.71 ml (21.11 mmoles) of pyridine and 0.17 g (1.41 moles) of N,N-dimethylaminopyridine in 15 ml of dichloromethane, cooled to about 0° C. The medium is maintained with stirring for 1 hr at 0° C. then for 1 hr at ambient temperature. The precipitate formed is filtered off then copiously rinsed with diisopropyl ether. After drying under vacuum at about 60° C., 3.12 g of the expected product are obtained in the form of a white solid used as such in the following stage.

Workup

  1. temperatureThe medium is maintained
  2. waitfor 1 hr at ambient temperature
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. washthen copiously rinsed with diisopropyl ether
  6. customAfter drying under vacuum at about 60° C.

Sources & evidence

ORD record
ord-3087eb836e0646e6a434bf625adb4676
Source dataset
uspto-grants-2013_03
Patent number
US08394787B2

Reaction notes

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