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

HRID 2247648노트

반응식

HRID 2247648 반응식
[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)[S: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.[OH-].[Na+].C(O)(=O)C.CO>O1CCOCC1.O>[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)[S: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

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 68526579HCID 68526579, 화합물

생성물 1

HCID 573984681-[(4-{5-[4-Phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methyl]azetidine-3-carboxylic acid수율 53.2%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of ethyl 1-[(4-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methyl]azetidine-3-carboxylate (70 mg, 0.13 mmol) that was obtained in Example 3 (3d) in dioxane (2 ml) was added a 1N aqueous solution of sodium hydroxide (0.39 ml, 0.39 mmol) with stirring, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, acetic acid (22 μl, 0.39 mmol) was added to the reaction mixture to quench the reaction, and the resulting mixture was evaporated in vacuo. To the residue thus obtained were added successively methanol (1 ml) and water (1 ml) with stirring, and 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 (34 mg) in a yield of 53% as a crystalline white solid.

후처리

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

출처 및 근거

ORD 기록
ord-8c425b50a0084e9ba730d41ab1dc3814
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687491B2

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