Ethanol → Sodium (3R,5S,E)-7-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-3,5-dihydroxy-6-heptenoate

HRID 2050592Notes

Reaction equation

HRID 2050592 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:31]([CH3:33])[CH3:32])[N:11](/[CH:20]=[CH:21]/[C@@H:22]([OH:30])[CH2:23][C@@H:24]([OH:29])[CH2:25][C:26]([OH:28])=[O:27])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(O)C.C(=O)([O-])O.[Na+:41]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:31]([CH3:33])[CH3:32])[N:11](/[CH:20]=[CH:21]/[C@@H:22]([OH:30])[CH2:23][C@@H:24]([OH:29])[CH2:25][C:26]([O-:28])=[O:27])[C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)=[CH:4][CH:3]=1.[Na+:41]

Participants

5

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 148498477-[4,5-Bis-(4-fluoro-phenyl)-2-isopropyl-imidazol-1-yl]-3,5-dihydroxy-hept-6-enoic acid

Product 1

HCID 23721969Sodium (3R,5S,E)-7-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-3,5-dihydroxy-6-heptenoateYield 104.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of (3R,5S,E)-7-[4,5-bis-(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-3,5-dihydroxy-6-heptenoic acid (200 mg) in sodium hydrogen carbonate (36.8 mg) and water (80 ml) was stirred at room temperature. After 19 h ethanol (20 ml) was added and the resulting clear solution stirred at room temperature. After 15 min the mixture was evaporated to dryness, the residue was dissolved in water (50 ml), filtered and then freeze dried to give the title compound (219 mg) as a white fluffy solid, [α]D +22.6° (C 0.53, H2O), δ(D2O) 1.20-1.55, 1.55-1.78 (m, 2H, CH(OH)CH2CH(OH)), 1.33 (d, J 7 Hz, 6H, CH(CH3)2), 2.26 (d, J 7 Hz, 2H, CH2CO2Na), 3.28 (septet, J 7 Hz, 1H, --CH(CH3)2, 3.67 (m, 1H, =CHCH(OH)CH2CH(OH)). 4.35 (m, 1H, CH=CHCH(OH)), 5.49 (dd, J 14 Hz and 7 Hz, 1H, NCH=CH), 6.72 (d, J 14 Hz, 1H, NCH=CH), 6.97 (t, 9 Hz, 2H, C-3 and C-5 protons of 4-fluorophenyl), 6.90-7.40 (m, 6H, aromatics).

Workup

  1. stirringthe resulting clear solution stirred at room temperature
  2. customAfter 15 min the mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in water (50 ml)
  4. filtrationfiltered
  5. customfreeze dried

Sources & evidence

ORD record
ord-fa110642dfe64d67b3efed50cb47cfb2
Source dataset
uspto-grants-1991_05
Patent number
US05013749

Reaction notes

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