Hydrochloric Acid → 2-(3-(4-(3-p-Tolylureido)phenyl)isoxazole-5-carboxamido)acrylic acid

HRID 75836노트

반응식

HRID 75836 반응식
[C:1]1([CH3:31])[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:30])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[C:19]([C:21]([NH:23][C:24](=[CH2:29])[C:25]([O:27]C)=[O:26])=[O:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)=[CH:3][CH:2]=1.O.O.[OH-].[Li+].Cl>C1COCC1>[C:1]1([CH3:31])[CH:2]=[CH:3][C:4]([NH:7][C:8](=[O:30])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[C:19]([C:21]([NH:23][C:24](=[CH2:29])[C:25]([OH:27])=[O:26])=[O:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67353451HCID 67353451, 화합물

생성물 1

HCID 673532812-(3-(4-(3-p-Tolylureido)phenyl)isoxazole-5-carboxamido)acrylic acid수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 2-(3-(4-(3-p-tolylureido)phenyl)isoxazole-5-carboxamido)acrylate (125 mg, 0.298 mmol) was dissolved in THF and water in 2:1 ratio. Lithium hydroxide monohydrate (19 mg, 0.447 mmol) was added and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. Organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. Crude compound was purified by washing with methanol to get 60 mg (50%) white solid as the required compound. MS: ES (+): m/z 407(M+1); 1HNMR (DMSO-d6, 300 MHz) δ: 9.732 (s, 1H), 8.989 (s, 1H), 8.714 (s, 1H), 7.894 (d, 2H), 7.784 (s, 1H), 7.638 (d, 2H), 7.377 (d, 2H), 7.121 (d, 2H), 6.232 (s, 1H), 5.921 (s, 1H), 5.918 (s, 3H).

후처리

  1. extractionextracted with EtOAc
  2. customOrganic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customCrude compound was purified
  6. washby washing with methanol

출처 및 근거

ORD 기록
ord-0951b442520e458eb5b4c668149fce9a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835428B2

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