Lithium Hydroxide → HCID 86707796、化合物

HRID 2174382ノート

反応式

HRID 2174382 の反応式
C[O:2][C:3]([CH:5]1[CH2:8][N:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH2:19][C:18]([C:24]4[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=4)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=3)=[CH:11][CH:10]=2)[CH2:6]1)=[O:4].[OH-].[Li+]>C1COCC1.CO.O>[Cl:32][C:26]1[CH:25]=[C:24]([C:18]2([C:20]([F:21])([F:23])[F:22])[O:17][N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([N:7]4[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:8]4)=[CH:10][CH:11]=3)[CH2:19]2)[CH:29]=[C:28]([Cl:30])[C:27]=1[Cl:31]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 86707795HCID 86707795、化合物

生成物 1

HCID 86707796HCID 86707796、化合物収率 85%

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

To a stirred suspension of 1-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid methyl ester (Preparation 11, 1.91 g, 3.77 mmol) in THF:MeOH:H2O (1:1:1, 60 mL) was added lithium hydroxide (0.791 g, 18.87 mmol) at room temperature and stirred at room temperature for 24 hours. After consumption of starting material, reaction mixture was concentrated in vacuo; suspension was diluted with water (20 mL) and acidified with 1N HCl up to pH ˜4. Acidified aqueous layer was extracted with ethyl acetate (5×50 mL). Combined organic layer washed with brine (150 mL), dried over sodium sulphate and evaporated under reduced pressure to afford yellow semi solid, which was triturated with chloroform:n-pentane (1:9) to afford yellow solid (1.57 g, 85%). 1H NMR (400 MHz, DMSO) δ: 3.49-3.52 (m, 1H), 3.90 (t, 2H, J=6.7 Hz), 4.04 (t, 2H, J=8.12 Hz), 4.13-4.25 (m, 2H), 6.46 (d, 2H, J=8.64 Hz), 7.48 (d, 2H, J=8.6 Hz), 7.79 (s, 2H); LC-MS (M+H): =492.60.

後処理

  1. customAfter consumption of starting material, reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additionsuspension was diluted with water (20 mL)
  4. extractionAcidified aqueous layer was extracted with ethyl acetate (5×50 mL)
  5. washCombined organic layer washed with brine (150 mL)
  6. dry with materialdried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customto afford yellow semi solid, which
  9. customwas triturated with chloroform:n-pentane (1:9)

出典と根拠

ORDレコード
ord-1ddd6853d14d4e90b082c070d5711043
出典データセット
uspto-grants-2015_06
特許番号
US09061013B2

反応ノート

読み込み中…