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Sodium Hydroxide → 3-(5-{3-Methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}pyrid-2-yl)-propanoic acid

HRID 1017982
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HRID 1017982 반응식
C([O:3][C:4](=[O:36])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:35])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])=[O:24])=[C:18]([O:33][CH3:34])[CH:17]=2)=[CH:9][N:8]=1)C.[OH-].[Na+]>C(O)C>[CH3:34][O:33][C:18]1[CH:17]=[C:16]([CH2:15][C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([OH:36])=[O:3])=[N:8][CH:9]=2)=[O:35])[CH:21]=[CH:20][C:19]=1[NH:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32])=[O:24]
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참가 물질

4

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HCID 14798Sodium HydroxideHCID 541518273-(5-{3-Methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}pyrid-2-yl)-propanoic acid ethyl ester

생성물 1

HCID 120505263-(5-{3-Methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}pyrid-2-yl)-propanoic acid수율 54.7%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
50 °C

실험 절차

A stirred mixture of 3-(5-{3-methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}pyrid-2-yl)-propanoic acid ethyl ester [0.62 g, Reference Example 3(a)] and ethanol (40 ml) was treated with 4% aqueous sodium hydroxide solution (3.2 ml) and then heated to 50° C. After stirring at 50° C. for 7 hours, the reaction mixture was cooled and then left to stand at room temperature over night. The reaction mixture was partially concentrated in vacuo, washed with diethyl ether and then acidified to pH 1.0 by addition of hydrochloric acid (1M). The resultant white solid was collected, washed with water and then dried in vacuo. Recrystallisation from aqueous acetonitrile gave the title compound (0.32 g) as a white crystalline solid, m.p. 191-192° C. (with decomposition). MS: MH+ 463.

후처리

  1. temperaturethe reaction mixture was cooled
  2. waitleft
  3. waitto stand at room temperature over night
  4. concentrationThe reaction mixture was partially concentrated in vacuo
  5. washwashed with diethyl ether
  6. additionacidified to pH 1.0 by addition of hydrochloric acid (1M)
  7. customThe resultant white solid was collected
  8. washwashed with water
  9. customdried in vacuo
  10. customRecrystallisation from aqueous acetonitrile

출처 및 근거

ORD 기록
ord-7ab7f0a8dbbb477e8c6a93fe44f023fd
출처 데이터셋
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06479519B1

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