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

HRID 75852노트

반응식

HRID 75852 반응식
[CH3:1][CH:2]([CH3:38])[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](=[O:37])[C:24](=[O:36])[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)=[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]([CH3:38])[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](=[O:37])[C:24](=[O:36])[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[CH:27]=3)=[CH:18][CH:17]=2)[CH:12]=1)=[O:10])[C:4]([OH:6])=[O:5]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67353582Methyl 3-methyl-2-(3-(4-(2-oxo-2-(3-(trifluoromethyl)phenylamino) acetamido)phenyl)isoxazole-5-carboxamido)butanoate

생성물 1

HCID 673522193-Methyl-2-(3-(4-(2-oxo-2-(3-(trifluoromethyl)phenylamino) acetamido)phenyl)isoxazole-5-carboxamido)butanoic acid수율 22.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To methyl 3-methyl-2-(3-(4-(2-oxo-2-(3-(trifluoromethyl)phenylamino)acetamido) phenyl)isoxazole-5-carboxamido)butanoate (100 mg) in THF (2 ml) 1 M aqueous solution of Lithium hydroxide monohydrate (0.375 ml) was added and reaction mixture was stirred at RT for 6 hours. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. Organic layer was collected and dried over Na2SO4 and concentrated to obtain off white solid, which was crystallized from EtOAc to yield 22 mg (22%) of the title compound as white solid. MS (ES+): m/z 519 (M+1); 1HNMR (DMSO-d6; 300 MHz): δ 11.24 (s, 1H), 11.13 (s, 1H), 9.01 (d, 1H), 8.35 (dd, 1H), 8.16 (dd, 1H), 8.06 (d, 2H), 7.96 (d, 2H), 7.73 (s, 1H), 7.64 (m, 1H), 7.54 (dd, 1H), 4.28 (m, 1H), 2.23 (m, 1H), 0.98 (d, 6H).

후처리

  1. customreaction mixture
  2. extractionextracted with EtOAc
  3. customOrganic layer was collected
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto obtain off white solid, which
  7. customwas crystallized from EtOAc

출처 및 근거

ORD 기록
ord-40b056e5d68e4f66b7f46f43614f10ca
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835428B2

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