Lithium hydroxide, monohydrate → ((1S)-5-{3-[(3-methyl-1-benzofuran-6-yl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetic acid

HRID 2235875ノート

反応式

HRID 2235875 の反応式
C([O:3][C:4](=[O:30])[CH2:5][C@H:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:29]=[CH:28][C:23]4[C:24]([CH3:27])=[CH:25][O:26][C:22]=4[CH:21]=3)=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)C.O[Li].O>C1COCC1.O>[CH3:27][C:24]1[C:23]2[CH:28]=[CH:29][C:20]([O:19][CH2:18][CH2:17][CH2:16][O:15][C:11]3[CH:10]=[C:9]4[C:14](=[CH:13][CH:12]=3)[C@H:6]([CH2:5][C:4]([OH:30])=[O:3])[CH2:7][CH2:8]4)=[CH:21][C:22]=2[O:26][CH:25]=1

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 59300536ethyl ((1S)-5-{3-[(3-methyl-1-benzofuran-6-yl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

生成物 1

HCID 24776386((1S)-5-{3-[(3-methyl-1-benzofuran-6-yl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetic acid収率 22%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

To a solution of ethyl((1S)-5-{3-[(3-methyl-1-benzofuran-6-yl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (119 mg, 0.29 mmol) (Example 64) in THF (4.2 mL) was added a solution of LiOH.H2O (15 mg, 0.35 mmol) in water (1.4 mL). The mixture was stirred for 4 h at 45° C. and then 12 h at rt. The reaction mixture was concentrated under reduced pressure, water was added, and the aqueous phase was washed with a small volume of Et2O. The pH was adjusted to below 3 with HCl (1 N aqueous solution), and the aqueous phase was extracted with excess EtOAc. The combined EtOAc extracts were dried, filtered, and concentrated under reduced pressure to give 24 mg (22%) of the title compound as a solid. 1H NMR (300 MHz, CDCl3): δ 7.44-7.22 (m, 2H), 7.08 (d, 1H), 6.98 (s, 1H), 6.89 (d, 1H), 6.80 (s, 1H), 6.72 (d, 1H), 4.32-4.04 (m, 4H), 3.63-3.44 (m, 1H), 2.98-2.76 (m, 3H), 2.58-2.37 (m, 2H), 2.37-2.14 (m, 5H), 1.88-1.70 (m, 1H); LC-MS: RT=3.53 min, (M+H)+ 381.1.

後処理

  1. custom12 h
  2. customat rt
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water
  4. additionwas added
  5. washthe aqueous phase was washed with a small volume of Et2O
  6. extractionthe aqueous phase was extracted with excess EtOAc
  7. dry with materialThe combined EtOAc extracts were dried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-88836180ad8949c78427f3745ddeaca7
出典データセット
uspto-grants-2010_05
特許番号
US07714004B2

反応ノート

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