Lithium hydroxide, monohydrate → 2-(3-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxamido)acetic acid

HRID 1773818ノート

反応式

HRID 1773818 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:31]([F:34])([F:33])[F:32])[O:13][N:12]=[C:11]([C:14]3[S:18][C:17]([C:19]([NH:21][CH2:22][C:23]([O:25]C)=[O:24])=[O:20])=[C:16]4[CH2:27][CH2:28][CH2:29][CH2:30][C:15]=34)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.O[Li].O>CO.O>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2([C:31]([F:32])([F:34])[F:33])[O:13][N:12]=[C:11]([C:14]3[S:18][C:17]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])=[C:16]4[CH2:27][CH2:28][CH2:29][CH2:30][C:15]=34)[CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 71467510Methyl 2-(3-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxamido)acetate

生成物 1

HCID 714688182-(3-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxamido)acetic acid収率 82%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

Stir a mixture of methyl 2-(3-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxamido)acetate (534 mg, 1.0 mmol) and LiOH—H2O (168 mg, 4.0 mmol) in MeOH (20 mL) and water (5 mL) at room temperature for overnight. After removal of organic solvent under vacuum, dilute the residue with ice water (10 mL). Acidify the aqueous mixture with conc. HCl to pH=1, and extract the resultant mixture with EtOAc (15 mL×3). The combined organic layers are washed brine, dried over anhydrous Na2SO4 and concentrated under vacuum. Purify the residue by silica gel chromatograph (PE:EtOAc 1:1) to afford 2-(3-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxamido)acetic acid as a pale yellow solid (427 mg, 82.0%). MS (m/z): 521 (M+1).

後処理

  1. customAfter removal of organic solvent under vacuum
  2. additiondilute the residue with ice water (10 mL)
  3. extractionextract the resultant mixture with EtOAc (15 mL×3)
  4. washThe combined organic layers are washed brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under vacuum
  7. customPurify the residue by silica gel chromatograph (PE:EtOAc 1:1)

出典と根拠

ORDレコード
ord-7cb33be2f5d8436e905c4a1f08c163b3
出典データセット
uspto-grants-2016_02
特許番号
US09255111B2

反応ノート

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