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

HRID 2247643노트

반응식

HRID 2247643 반응식
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[O:22][C:21]([CH2:23][N:24]5[CH2:27][CH:26]([C:28]([O:30]CC)=[O:29])[CH2:25]5)=[CH:20][CH:19]=4)[N:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.O.[OH-].[Li+].C(O)(=O)C>O.CO>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[O:22][C:21]([CH2:23][N:24]5[CH2:27][CH:26]([C:28]([OH:30])=[O:29])[CH2:25]5)=[CH:20][CH:19]=4)[N:14]=3)=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68524364HCID 68524364, 화합물

생성물 1

HCID 119778161-({5-[5-(4-Cyclohexylphenyl)-1,2,4-oxadiazol-3-yl]-2-furyl}methyl)azetidine-3-carboxylic acid수율 56.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a solution of ethyl 1-({5-[5-(4-cyclohexylphenyl)-1,2,4-oxadiazol-3-yl]-2-furyl}methyl)azetidine-3-carboxylate (0.23 g, 0.53 mmol) that was obtained in Example 2 (2d) in a mixed solvent of tetrahydrofuran (0.50 ml), methanol (0.50 ml) and water (0.50 ml) was added lithium hydroxide monohydrate (50 mg, 1.2 mmol) with stirring, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, acetic acid (65 μl, 1.2 mmol) was added to the reaction mixture to quench the reaction. 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 (122 mg) in a yield of 56% 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. customThe white solid precipitated
  6. filtrationwas collected by filtration
  7. washwashed with a mixed solvent of water and methanol (3:7)
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-79546d31bb11429d8d3129d7ea71e82d
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687491B2

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