Sodium Hydroxide → 7-[4,5-Bis-(4-fluoro-phenyl)-2-isopropyl-imidazol-1-yl]-3,5-dihydroxy-hept-6-enoic acid

HRID 2050591Notes

Reaction equation

HRID 2050591 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:35]([CH3:37])[CH3:36])[N:11](/[CH:20]=[CH:21]/[C@@H:22]([OH:34])[CH2:23][C@@H:24]([OH:33])[CH2:25][C:26]([O:28]C(C)(C)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+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:35]([CH3:37])[CH3:36])[N:11](/[CH:20]=[CH:21]/[C@@H:22]([OH:34])[CH2:23][C@@H:24]([OH:33])[CH2:25][C:26]([OH: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

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 148498511,1-dimethyleth-1-yl (3R,5S,E)-7-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-3,5-dihydroxy-6-heptenoate

Product 1

HCID 148498477-[4,5-Bis-(4-fluoro-phenyl)-2-isopropyl-imidazol-1-yl]-3,5-dihydroxy-hept-6-enoic acidYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,1-dimethyleth-1-yl (3R,5S,E)-7-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-3,5-dihydroxy-6-heptenoate (726 mg) in redistilled THF (40 ml) was treated with 0.1M aqueous sodium hydroxide solution (14.5 ml). After 1/2 h the mixture was concentrated to ca. 10 ml and then diluted with water (50 ml). The mixture was acidified to pH 2 with 2N-hydrochloric acid, brought back to pH 4 with aqueous sodium hydrogen carbonate solution, ammonium sulphate added and then the mixture was extracted with ethyl acetate (3×50 ml). The combined extracts were dried and concentrated to ca. 4 ml when a solid crystallised. The crystals were collected and dried to give the title compound (500 mg), m.p. 172°-3° C., [α]D +15.7° (c 1.02, DMSO), (RS:SR=99.5:0.5).

Workup

  1. concentrationAfter 1/2 h the mixture was concentrated to ca. 10 ml
  2. additiondiluted with water (50 ml)
  3. additionadded
  4. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
  5. customThe combined extracts were dried
  6. concentrationconcentrated to ca. 4 ml when a solid
  7. customcrystallised
  8. customThe crystals were collected
  9. customdried

Sources & evidence

ORD record
ord-37e7fce340734737a6c0989aed8a8ad7
Source dataset
uspto-grants-1991_05
Patent number
US05013749

Reaction notes

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