HCID 67078524, compound → HCID 18767630, compound

HRID 480106Notes

Reaction equation

HRID 480106 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 1

HCID 67078524HCID 67078524, compound

Product 1

HCID 18767630HCID 18767630, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

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 cone. HCl and then extracted with EtOAc. The combined EtOAc extracts were washed with saturated NaHCO3, H2O and brine, and dried (MgSO4). 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. extractionHCl and then extracted with EtOAc
  5. washThe combined EtOAc extracts were washed with saturated NaHCO3, H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and evaporation
  8. washeluting with 3:2 EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-96ebc9e94784469f976a3a23b8275785
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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