Trifluoroacetic acid → 6-[(4S)-4-Amino-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 1847013Notes

Reaction equation

HRID 1847013 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.O.C(OC(=O)[NH:22][C@H:23]1[CH2:27][C:26](=[O:28])[N:25]([C:29]2[CH:30]=[CH:31][C:32]3[O:33][CH2:34][C:35](=[O:39])[NH:36][C:37]=3[N:38]=2)[CH2:24]1)(C)(C)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[NH2:22][C@@H:23]1[CH2:24][N:25]([C:29]2[CH:30]=[CH:31][C:32]3[O:33][CH2:34][C:35](=[O:39])[NH:36][C:37]=3[N:38]=2)[C:26](=[O:28])[CH2:27]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 22392675Trifluoroacetic acid waterHCID 86724943[(3S)-5-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

Product 1

HCID 867249446-[(4S)-4-Amino-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-oneYield 80.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Aqueous trifluoroacetic acid (trifluoroacetic acid/water=95:5, v/v, 3.5 ml) was added to [(3S)-5-oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester (148 mg, 0.425 mmol) and the mixture was stirred in an ice bath for 2 hours. The reaction solution was diluted with ethyl acetate, neutralized by adding a saturated sodium hydrogen carbonate aqueous solution and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica gel, chloroform/methanol) to yield 84.5 mg (80%) of the title compound in the form of a colorless solid.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, chloroform/methanol)

Sources & evidence

ORD record
ord-38c3fc2a3dba4760a751f2a5fd488d4e
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

Loading…