Hydrochloric Acid → 3-Methyl-2-(3-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl) isoxazole-5-carboxamido)butanoic acid

HRID 75831노트

반응식

HRID 75831 반응식
[CH3:1][CH:2]([CH3:36])[CH:3]([NH:8][C:9]([C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[O:24])=[CH:18][CH:17]=2)[CH:12]=1)=[O:10])[C:4]([O:6]C)=[O:5].O.[OH-].[Li+].Cl>C1COCC1>[CH3:1][CH:2]([CH3:36])[CH:3]([NH:8][C:9]([C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:34])([F:33])[F:35])=[CH:30][CH:31]=3)=[O:24])=[CH:20][CH:21]=2)[CH:12]=1)=[O:10])[C:4]([OH:6])=[O:5]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67352407Methyl 3-methyl-2-(3-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl)isoxazole-5-carboxamido)butanoate

생성물 1

HCID 673534913-Methyl-2-(3-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl) isoxazole-5-carboxamido)butanoic acid수율 76.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To Methyl 3-methyl-2-(3-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl)isoxazole-5-carboxamido)butanoate (250 mg) dissolved in THF (5 ml) was added 1 M aqueous solution of Lithium hydroxide monohydrate (1 ml) and stirred at RT for 14 h. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. Organic layer was separated, dried over. Na2SO4 and concentrated under reduced pressure to get off white solid which was crystallized from EtOAc to yield 185 mg (76%) white solid. MS (ES+): m/z 491 (M+1); 1H NMR (DMSO-d6, 300 MHz): δ 12.82 (bs, 1H), 9.22 (s, 1H), 9.12 (s, 1H), 8.93 (d, 1H), 7.85 (d, 2H), 7.68 (s, 1H), 7.65 (d, 2H), 7.61 (d, 2H), 7.56 (d, 2H), 4.26 (m, 1H), 2.21 (m, 1H), 0.95 (d, 6H).

후처리

  1. extractionextracted with EtOAc
  2. customOrganic layer was separated
  3. customdried over
  4. concentrationNa2SO4 and concentrated under reduced pressure
  5. customto get off white solid which
  6. customwas crystallized from EtOAc

출처 및 근거

ORD 기록
ord-087fed4df0044aa59dcdaa948153bb64
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835428B2

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