[5-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-yl]carbamic acid benzyl ester → 6-(4-Amino-2-oxopyrrolidin-1-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 1847010Notes

Reaction equation

HRID 1847010 reaction equation
C(OC(=O)[NH:10][CH:11]1[CH2:15][C:14](=[O:16])[N:13]([C:17]2[CH:18]=[CH:19][C:20]3[O:21][CH2:22][C:23](=[O:27])[NH:24][C:25]=3[N:26]=2)[CH2:12]1)C1C=CC=CC=1>CO.[Pd]>[NH2:10][CH:11]1[CH2:12][N:13]([C:17]2[CH:18]=[CH:19][C:20]3[O:21][CH2:22][C:23](=[O:27])[NH:24][C:25]=3[N:26]=2)[C:14](=[O:16])[CH2:15]1

Participants

4

Reactant 1

HCID 86724940[5-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-yl]carbamic acid benzyl ester

Product 1

HCID 867249416-(4-Amino-2-oxopyrrolidin-1-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-oneYield 92.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

[5-oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-yl]carbamic acid benzyl ester (66.8 mg, 0.175 mmol) was dissolved in methanol (4 ml), 10% palladium on carbon (50% wet, 50 mg) was added thereto and catalytic hydrogenation was carried out at room temperature for 1 hour and at 50° C. for 45 minutes. The catalyst was removed by filtration and washed with methanol, and the filtrate and washings were concentrated under reduced pressure to yield 40.1 mg (92%) of the title compound in the form of a colorless solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. concentrationthe filtrate and washings were concentrated under reduced pressure

Sources & evidence

ORD record
ord-b492e53b6bd14c55945735617dc20da5
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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