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

HRID 892975
ノート
印刷プレビュー

反応式

HRID 892975 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water
溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d62b6934ba6f440fb9401377c35b0279
出典データセット
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05120848

反応ノート

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