Acetic Acid → 1-({4-[3-(4-Isobutylphenyl)isoxazol-5-yl]-2-thienyl}methyl)azetidine-3-carboxylic acid

HRID 2247682노트

반응식

HRID 2247682 반응식
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([C:16]3[CH:17]=[C:18]([CH2:21][N:22]4[CH2:25][CH:24]([C:26]([O:28]CC)=[O:27])[CH2:23]4)[S:19][CH:20]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].CO.C(O)(=O)C>O1CCOCC1.O>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([C:16]3[CH:17]=[C:18]([CH2:21][N:22]4[CH2:25][CH:24]([C:26]([OH:28])=[O:27])[CH2:23]4)[S:19][CH:20]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 68525245Ethyl 1-({4-[3-(4-isobutylphenyl)isoxazol-5-yl]-2-thienyl}methyl)azetidine-3-carboxylate

생성물 1

HCID 592180241-({4-[3-(4-Isobutylphenyl)isoxazol-5-yl]-2-thienyl}methyl)azetidine-3-carboxylic acid수율 80.2%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of ethyl 1-({4-[3-(4-isobutylphenyl)isoxazol-5-yl]-2-thienyl}methyl)azetidine-3-carboxylate (0.47 g, 1.1 mmol) that was obtained in Example 9 (9h) in 1,4-dioxane (15 ml) was added a 1N aqueous solution of sodium hydroxide (3.3 ml, 3.3 mmol) at 0° C. with stirring, and then the resulting mixture was stirred at room temperature for 30 minutes. After adding methanol (15 ml) and water (5 ml) to the reaction mixture, the resulting mixture was heated under stirring until the white solid precipitated was dissolved, and then acetic acid (0.19 ml, 3.3 mmol) was added. The white solid precipitated was collected by filtration using a Kiriyama funnel, washed with methanol and dried in vacuo to afford the title compound (0.35 g) in a yield of 78% as a white crystalline solid.

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. temperaturethe resulting mixture was heated
  3. stirringunder stirring until the white solid
  4. customprecipitated
  5. dissolutionwas dissolved
  6. customThe white solid precipitated
  7. filtrationwas collected by filtration
  8. washwashed with methanol
  9. customdried in vacuo

출처 및 근거

ORD 기록
ord-5f56c01e3ac74179b718b38896e0463f
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687491B2

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