Sodium Hydroxide → HCID 18767630, compound

HRID 2105637Notes

Reaction equation

HRID 2105637 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[C:3]=1[NH:16][C:17]([C:19]12[CH2:26][C:23]([CH2:27][OH:28])([CH2:24][CH2:25]1)[CH2:22][CH2:21][CH2:20]2)=O.[OH-].[Na+]>CO>[OH:28][CH2:27][C:23]12[CH2:26][C:19]([C:17]3[NH:16][C:3]4[C:4](=[O:15])[N:5]([CH2:12][CH2:13][CH3:14])[C:6](=[O:11])[N:7]([CH2:8][CH2:9][CH3:10])[C:2]=4[N:1]=3)([CH2:25][CH2:24]1)[CH2:20][CH2:21][CH2:22]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67078524HCID 67078524, compound

Product 1

HCID 18767630HCID 18767630, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-hydroxymethyl-bicyclo[3.2.1]octane-1-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide (0.51 mmol, 0.20 g) in 20°% NaOH (2.0 ml) and MeOH (10.0 ml) was stirred and refluxed overnight. The reaction was cooled to room temperature and then concentrated to remove MeOH. The aqueous was acidified (pH 2-3) with conc. HCl and then extracted with EtOAc. The combined EtOAc extracts were washed with saturated NaHCO3, H2O and brine, and dried (MgSQ4). Filtration and evaporation followed by flash chromatography eluting with 3:2 EtOAc/CH2Cl2 provided title compound (0:077 g, 40%) as an oil. 13C NMR (100 MHz, CDCl3): 11.53 (q), 11.74 (q), 20.26 (t), 21.71 (t), 31.62 (t) 34.15 (t), 37.29 (t), 43.49 (s), 45.54 (t), 45.67 (t), 46.14 (t). 46.90 (t), 70.51 (t), 71.11 (s), 107.03 (s), 149.25 (s), 151.54 (s), 155.88 (s), 162.58 (s).

Workup

  1. temperaturerefluxed overnight
  2. concentrationconcentrated
  3. customto remove MeOH
  4. extractionextracted with EtOAc
  5. washThe combined EtOAc extracts were washed with saturated NaHCO3, H2O and brine
  6. customdried (MgSQ4)
  7. filtrationFiltration and evaporation
  8. washeluting with 3:2 EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-495db4c7208c4c3d81337acf75cc5c62
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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