Water → Cp-195543

HRID 1278946ノート

反応式

HRID 1278946 の反応式
CC(C)(C)C[O:4][C:5](=[O:34])[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[C:16]1[CH:25]=[C:24]2[C:19]([C@H:20]([OH:33])[C@@H:21]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:22][O:23]2)=[CH:18][CH:17]=1.[OH-].[Na+].O>C(O)(C)C>[CH2:26]([C@@H:21]1[C@@H:20]([OH:33])[C:19]2[C:24](=[CH:25][C:16]([C:7]3[CH:8]=[C:9]([C:12]([F:15])([F:13])[F:14])[CH:10]=[CH:11][C:6]=3[C:5]([OH:34])=[O:4])=[CH:17][CH:18]=2)[O:23][CH2:22]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

参加物

5

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 10918078(3S,4R)-2-(3-benzyl-4-hydroxy-chroman-7-yl)-4-trifluoromethyl-benzoic acid 2,2-dimethylpropyl ester

生成物 1

HCID 9823886Cp-195543収率 50.3%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A solution of (3S, 4R)-2-(3-benzyl-4-hydroxy-chroman-7-yl)-4-trifluoromethyl-benzoic acid 2,2-dimethyl-propyl ester (2.34 g, 4.69 mmol) in isopropyl alcohol (23 mL) was treated with 10% aqueous sodium hydroxide (2.3 mL, 6.4 mmol) and heated at reflux for 3 hours. The reaction mixture was cooled to ambient temperature, poured into water (34 mL), and extracted with hexanes (23 mL) and isopropyl ether (13 mL). The aqueous layer was separated and extracted with hexanes (23 mL) and isopropyl ether (13 mL), adjusted to pH 2 with 6N aqueous hydrochloric acid, and extracted with ethyl acetate (two times 40 mL). The combined ethyl acetate extracts were washed with brine (40 mL), dried over magnesium sulfate, filtered and concentrated to a white foam which was recrystallized from toluene/hexanes. The resulting solids were filtered and washed with hexanes, and the wet cake was stirred with hexanes (20 mL) for 1 hour. The mixture was filtered, and the resulting solids were dried under vacuum to provide 1.01 g (50% yield) of (3S, 4R)-2-(3-benzyl-4-hydroxy-chroman-7-yl)-4-trifluoromethyl-benzoic acid as a white solid: 1H NMR (400 MHz, CDCl3) 67 8.00 (d, J=8.1 Hz, 1H), 7.67 (d, J=8.1 Hz, 1 H), 7.64 (s, 1 H), 7.18-7.36 (m, 6H), 6.91 (dd, J=7.9, 1.7 Hz, 1 H), 6.86 (d, J=1.7 Hz, 1 H), 4.53 (d, J=4.2 Hz, 1 H), 4.24 (dd, J=11.2, 2.7 Hz, 1 H), 3.97 (dd, J=11.0, 4.0 HZ, 1 H), 2.76 (dd, J=13.9, 6.4 Hz, 1 H), 2.53 (dd, J=13.7, 9.3 Hz, 1 H), 2.24-2.26 (m, 1 H).

後処理

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. extractionextracted with hexanes (23 mL) and isopropyl ether (13 mL)
  4. customThe aqueous layer was separated
  5. extractionextracted with hexanes (23 mL) and isopropyl ether (13 mL)
  6. extractionextracted with ethyl acetate (two times 40 mL)
  7. washThe combined ethyl acetate extracts were washed with brine (40 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to a white foam which
  11. customwas recrystallized from toluene/hexanes
  12. filtrationThe resulting solids were filtered
  13. washwashed with hexanes
  14. filtrationThe mixture was filtered
  15. customthe resulting solids were dried under vacuum

出典と根拠

ORDレコード
ord-6a641687541548149a454bd7be40d753
出典データセット
uspto-grants-2002_09
特許番号
US06444826B1

反応ノート

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