Pyridine → (R)-methyl 2-(3-(4-(2-fluorophenylsulfonamido)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate

HRID 75839

반응식

HRID 75839 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([NH:15][C@H:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[S:37]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([NH:15][C@H:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[O:10][N:9]=2)=[CH:4][CH:3]=1)(=[O:39])=[O:38]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 1377612-Fluorobenzenesulphonyl chlorideHCID 67352792(R)-methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-methylbutanoate

생성물 1

HCID 67355864(R)-methyl 2-(3-(4-(2-fluorophenylsulfonamido)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 500 mg (1.57 mmol) of (R)-methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-methylbutanoate (example 151, step 3) in DCM, 1.2 eq of pyridine was added and stirred for 10 minutes, then 368 mg (1.89 mmol) 2-fluorobenzene-1-sulfonyl chloride was added and the reaction mixture was stirred for 3 hours. DCM was removed under vacuum, the reaction mixture was washed with 1NHCl and extracted with EtOAc. The organic layer was concentrated and purified by precipitation using DCM and petroleum ether to yield 410 mg (86%) of title compound. MS (ESI): m/z 476(M+H)+; 1HNMR (DMSO-d6, 300 MHz): δ 11.039 (s, 1H), 9.215 (d, 1H), 7.942 (m, 1H), 7.805 (d, 2H), 7.718 (m, 1H), 7.625 (s, 1H), 7.465 (m, 2H), 7.271(d, 2H), 4.314 (t, 1H), 3.690 (s, 3H), 2.228 (m, 1H), 0.971 (d, 6H).

후처리

  1. stirringthe reaction mixture was stirred for 3 hours
  2. customDCM was removed under vacuum
  3. washthe reaction mixture was washed with 1NHCl and
  4. extractionextracted with EtOAc
  5. concentrationThe organic layer was concentrated
  6. custompurified by precipitation

출처 및 근거

ORD 기록
ord-55309ba916b148068439f137b36f3df1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835428B2

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