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 2247638노트

반응식

HRID 2247638 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)[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

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 971Oxalic AcidHCID 168937Lithium hydroxide, monohydrateHCID 68528577HCID 68528577, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-21928229e08649829e1c79204a0db8b5
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687491B2

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