Sodium Hydroxide → HCID 9800112, compound

HRID 480137Notes

Reaction equation

HRID 480137 reaction equation
C[O:2][C:3]([C:5]12[CH:12]3[CH:7]4[C:8]5([C:13](=O)[NH:14][C:15]6[C:16](=[O:29])[N:17]([CH2:26][CH2:27][CH3:28])[C:18](=[O:25])[N:19]([CH2:22][CH2:23][CH3:24])[C:20]=6[NH2:21])[CH:11]3[CH:10]1[CH:9]5[CH:6]24)=[O:4].[OH-].[Na+]>CO>[O:25]=[C:18]1[N:19]([CH2:22][CH2:23][CH3:24])[C:20]2[N:21]=[C:13]([C:8]34[CH:11]5[CH:10]6[CH:9]3[CH:6]3[CH:7]4[CH:12]5[C:5]36[C:3]([OH:2])=[O:4])[NH:14][C:15]=2[C:16](=[O:29])[N:17]1[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67078075HCID 67078075, compound

Product 1

HCID 9800112HCID 9800112, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-cubane-1-carboxylic acid methyl ester (400 mg, 0.966 mmol) in MeOH (20 ml) was added 4 ml of a 20% aq. NaOH solution and the resulting turbid mixture was heated at reflux overnight (12 h). The cool reaction mixture was concentrated in vacuo, diluted with several small ice chips and acidified by the dropwise addition of concentrated HCl. The resulting white precipitate was collected, dried, and washed with ether to give a white solid (280 mg, 76%). 1H NMR (400 MHz, DMSO-d6) δ 1.05 (coincident t, 6H), 1.70 (m, 2H), 1.83 (m, 2H), 3.99 (m, 2H), 4.08 (m, 2H), 4.27 (m, 3H), 4.38 (m, 3H). MS: 383 (MH+).

Workup

  1. temperaturethe resulting turbid mixture was heated
  2. temperatureat reflux overnight (12 h)
  3. customThe cool reaction mixture
  4. concentrationwas concentrated in vacuo
  5. additiondiluted with several small ice chips
  6. additionacidified by the dropwise addition of concentrated HCl
  7. customThe resulting white precipitate was collected
  8. customdried
  9. washwashed with ether

Sources & evidence

ORD record
ord-37669ea1e2454934baef1d6a8f86a58c
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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