p-Toluenesulfonic acid → HCID 21714039, compound

HRID 650246Notes

Reaction equation

HRID 650246 reaction equation
C(OC([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH:11]([C:21](=[O:23])[CH3:22])[O:10]C1(C)C)=O)(C)(C)C.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32]([OH:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(O)C>[C:26]1([CH3:36])[CH:27]=[CH:28][C:29]([S:32]([OH:35])(=[O:33])=[O:34])=[CH:30][CH:31]=1.[NH2:8][CH:12]([CH:11]([OH:10])[C:21](=[O:23])[CH3:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 21714067HCID 21714067, compound

Product 1

HCID 21714039HCID 21714039, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-t-Butyloxycarbonyl-2,2-dimethyl-5-(1-oxoethyl)-4-(3-fluorophenyl)methyloxazolidine (17.94 g, 51.1 mmol) was dissolved in ethanol (180 ml), and p-toluenesulfonic acid.1H2O (10.7 g, 56.2 mmol) was added to it and the mixture was heated under reflux for 2 hours with stirring. The reaction solution was concentrated under reduced pressure, and the resulting residue was dried with a vacuum pump (2 mmHg) at 50° C., whereby crude 2-amino-1-(3-fluorophenyl)-3-hydroxy-4-oxopentane p-toluenesulfonate (21.5 g) was obtained as solid. This solid was subjected without further purification to the subsequent condensation reaction.

Workup

  1. addition1H2O (10.7 g, 56.2 mmol) was added to it
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. customthe resulting residue was dried with a vacuum pump (2 mmHg) at 50° C.

Sources & evidence

ORD record
ord-cc6ca4428ac0489684d1e550bd26d311
Source dataset
uspto-grants-2001_08
Patent number
US06271238B1

Reaction notes

Loading…