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

HRID 1466002Notes

Reaction equation

HRID 1466002 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:14]([C:17]1[CH:21]=[C:20]([CH2:22][OH:23])[O:19][N:18]=1)(=[O:16])[NH2:15].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:23][CH2:22][C:20]1[O:19][N:18]=[C:17]([C:14](=[O:16])[NH2:15])[CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 80272465-(Hydroxymethyl)-1,2-oxazole-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 mmol) of 4-nitrophenyl chloroformate are added in small portions to a solution, cooled to approximately 0° C., of 2.00 g (14.07 mmol) of 3-carbamoylisoxazol-5-ylmethanol, 1.71 ml (21.11 mmol) of pyridine and 0.17 g (1.41 mmol) of N,N-dimethylaminopyridine in 15 ml of dichloromethane. The medium is kept stirred at 0° C. for 1 hour and then at ambient temperature for 1 hour. The precipitate formed is filtered off and then copiously rinsed with diisopropyl ether. After drying under vacuum at approximately 60° C., 3.12 g (72%) of the expected product are obtained in the form of a white solid used as is in the following stage.

Workup

  1. waitat ambient temperature for 1 hour
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washcopiously rinsed with diisopropyl ether
  5. customAfter drying under vacuum at approximately 60° C.

Sources & evidence

ORD record
ord-74669c2a7f454a1593f7bd8e31dad2af
Source dataset
uspto-grants-2015_04
Patent number
US09000010B2

Reaction notes

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