Sodium Acetate → 5-Hydroxy-1-(2-cyclohexyl-2-acetoxyethylideneamino)-3-propylhexahydrocyclopenta[d]imidazole-2(1H)-one

HRID 1885900Notes

Reaction equation

HRID 1885900 reaction equation
[NH2:1][N:2]1[CH:6]2[CH2:7][CH:8]([OH:10])[CH2:9][CH:5]2[N:4]([CH2:11][CH2:12][CH3:13])[C:3]1=[O:14].[C:15]([O:18][CH:19]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH:20]=O)(=[O:17])[CH3:16].C([O-])(=O)C.[Na+]>CO>[OH:10][CH:8]1[CH2:7][CH:6]2[N:2]([N:1]=[CH:20][CH:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[O:18][C:15](=[O:17])[CH3:16])[C:3](=[O:14])[N:4]([CH2:11][CH2:12][CH3:13])[CH:5]2[CH2:9]1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 109869602-Cyclohexyl-2-acetoxyacetaldehydeHCID 198784021-amino-3-propyl-5-hydroxyhexahydrocyclopenta[d]imidazole-2(1H)-one

Product 1

HCID 543417855-Hydroxy-1-(2-cyclohexyl-2-acetoxyethylideneamino)-3-propylhexahydrocyclopenta[d]imidazole-2(1H)-oneYield 117.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

A solution of the compound of step (g) (5.0 g) and 2-acetoxy-2-cyclohexylacetaldehyde (Ross et al, J. Med. Chem., 22, 412 (1979), 6.0 g) in methanol (175 ml) containing sodium acetate (3.64 g) was stirred at 15° C. under a nitrogen atmosphere for 16 hours. The alcohol was removed in vacuo and water (100 ml) and chloroform (100 ml) added. The organic phase was separated and washed with brine (100 ml), then dried over anhy. sodium sulphate. Filtration and concentration of the filtrate in vacuo gave a yellow oil (10.8 g).

Workup

  1. customThe alcohol was removed in vacuo and water (100 ml) and chloroform (100 ml)
  2. additionadded
  3. customThe organic phase was separated
  4. washwashed with brine (100 ml)
  5. customdried over anhy
  6. filtrationFiltration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-8b4f97a634b142dd8f84a9e8803c0ffd
Source dataset
uspto-grants-1992_09
Patent number
US05147885

Reaction notes

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