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

HRID 892972Notes

Reaction equation

HRID 892972 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:32]([CH3:34])[CH3:33])[N:11](/[CH:20]=[CH:21]/[C@@H:22]([OH:31])[CH2:23][C@@H:24]([OH:30])[CH2:25][C:26]([O:28]C)=[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.[OH-].[Na+:36]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:32]([CH3:34])[CH3:33])[N:11](/[CH:20]=[CH:21]/[C@@H:22]([OH:31])[CH2:23][C@@H:24]([OH:30])[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+:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14849841Methyl (3R,5S,E)-7-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-3,5-dihydroxy-6-heptenoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl (3R,5S,E)-7-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-3,5-dihydroxy-6-heptenoate (34.4 mg) in dry THF (2 ml) was treated with aqueous sodium hydroxide solution (0.1M 0.660 ml). After 5 minutes, the solution was concentrated and the aqueous residue was diluted with water (9 ml) and the solution washed with ethyl acetate (4×). The solution was briefly evaporated and then freeze-dried to give the title compound (29.2 mg) as a white fluffy solid, [α]20 +16.7° (c 0.4, H2O); δ(D2O) 1.20-1.55, 1.55-1.85 (m, 2H, CH(OH)CH2CH(OH)), 1.34 (d, J 7 Hz, 6H, CH(CH3)2), 2.26 (d, J 7 Hz, 2H, CH2CO2Na), 3.30 (septet, J 7 Hz, 1H, CH(CH3)2), 3.67 (m, 1H, =CHCH(OH)CH2CH(OH)), 4.35 (m, 1H, CH=CHCH(OH)), 5.61 (dd, J 14 and 7 Hz, 1H, NCH=CH), 6.75 (d, J 14 Hz, 1H, NCH=CH), 7.01 (t, J 9 Hz, 2H, C-3 and C-5 protons of 4-(4-fluorophenyl)), 7.1-7.4 (m, 6H, aromatics).

Workup

  1. concentrationthe solution was concentrated
  2. additionthe aqueous residue was diluted with water (9 ml)
  3. washthe solution washed with ethyl acetate (4×)
  4. customThe solution was briefly evaporated
  5. customfreeze-dried

Sources & evidence

ORD record
ord-20a8eaac2af447e8aa1edc0f249e9363
Source dataset
uspto-grants-1992_06
Patent number
US05120848

Reaction notes

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