HCID 69978905, compound → HCID 131722970, compound

HRID 428382Notes

Reaction equation

HRID 428382 reaction equation
C[CH:2]([C:17]([OH:19])=[O:18])[CH2:3][CH2:4][CH2:5][N:6]1[C:11]2[NH:12][C:13](=[O:16])[N:14]=[CH:15][C:10]=2[CH2:9][CH2:8][O:7]1>[OH-].[Na+]>[NH4+:6].[C:17]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]2[NH:12][C:13](=[O:16])[N:14]=[CH:15][C:10]=2[CH2:9][CH2:8][O:7]1)([OH:19])=[O:18]

Participants

3

Reactant 1

HCID 69978905HCID 69978905, compound

Product 1

HCID 131722970HCID 131722970, compoundYield 112.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

1-(4-Methylcarboxybutyl)-3,4-dihydro-8H-pyrimido[4, 5-c][1,2]oxazine-7-one (13.5) (0.42 g, 1.57 mmol) was dissolved in 1M aqueous sodium hydroxide solution (10 ml) and stirred for 2 hours. The mixture was applied to an ion exchange column of Dowex 50 WX8-200. This was eluted with water and the product recovered using 2M aqueous ammonia solution. The solution volume was reduced and then freeze-dried to yield a white solid (0.24 g, 60.4%). The product appeared as a single spot when analysed in the following thin-layer chromatography systems: Silica gel eluted with chloroform:methanol (7:3) and butan-1-ol: water, glacial acetic acid (12:5:3); Silica gel impregnated with ODS eluted with methanol:water:glacial acetic acid (80:20:1); Cellulose eluted with butan-1-ol:water:glacial acetic acid (12:5:3). The structure was confirmed by mass spectroscopy and proton NMR.

Workup

  1. washThis was eluted with water
  2. customthe product recovered
  3. customfreeze-dried

Sources & evidence

ORD record
ord-346345dd5d9b44dcb2baa45837586e92
Source dataset
uspto-grants-2001_11
Patent number
US06313286B1

Reaction notes

Loading…