Acetic Acid → 1-[(4-{5-[4-Phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-furyl)methyl]azetidine-3-carboxylic acid

HRID 2247638ノート

反応式

HRID 2247638 の反応式
[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]([CH2:26][N:27]5[CH2:30][CH:29]([C:31]([O:33]CC)=[O:32])[CH2:28]5)[O:24][CH:25]=4)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+].C(O)(=O)C.C(O)(=O)C(O)=O>CO.O.O1CCCC1>[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]([CH2:26][N:27]5[CH2:30][CH:29]([C:31]([OH:33])=[O:32])[CH2:28]5)[O:24][CH:25]=4)[N:17]=3)[S:10][C:11]=2[C:12]([F:14])([F:13])[F:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 971Oxalic AcidHCID 168937Lithium hydroxide, monohydrateHCID 68528577HCID 68528577、化合物

生成物 1

HCID 119777061-[(4-{5-[4-Phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-furyl)methyl]azetidine-3-carboxylic acid収率 43.1%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl 1-[(4-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-furyl)methyl]azetidine-3-carboxylate (0.20 g, 0.40 mmol) that was obtained in Example 1 (1f) in a mixed solvent of tetrahydrofuran (0.50 ml), methanol (0.50 ml) and water (0.50 ml) was added lithium hydroxide monohydrate (37 mg, 0.88 mmol) with stirring, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, acetic acid (48 μl, 0.88 mmol) was added to the reaction mixture to quench the reaction. Subsequently, to the resulting mixture was added a solution of oxalic acid (18 mg, 0.20 mmol) in methanol (0.5 ml) with stirring, and the resulting mixture was stirred for 30 minutes. The white solid precipitated was collected by filtration using a Kiriyama funnel, washed with a mixed solvent of water and methanol (3:7), and dried in vacuo to afford the title compound (82 mg) in a yield of 39% as a white crystalline solid.

後処理

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. stirringAfter stirring
  3. customto quench
  4. customthe reaction
  5. stirringwith stirring
  6. stirringthe resulting mixture was stirred for 30 minutes
  7. customThe white solid precipitated
  8. filtrationwas collected by filtration
  9. washwashed with a mixed solvent of water and methanol (3:7)
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-21928229e08649829e1c79204a0db8b5
出典データセット
uspto-grants-2010_03
特許番号
US07687491B2

反応ノート

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