Trifluoroacetic acid → (3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 627168노트

반응식

HRID 627168 반응식
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22](C(OC(C)(C)C)=O)[C@H:21]([CH2:31][O:32][CH3:33])[CH:20]=[C:19]1[C:34](=[O:38])[N:35]([CH3:37])[CH3:36])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:4][N:5]([C@@H:18]1[C:19]([C:34]([N:35]([CH3:37])[CH3:36])=[O:38])=[CH:20][C@@H:21]([CH2:31][O:32][CH3:33])[NH:22][CH2:23]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 89851960(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(dimethylcarbamoyl)-2-(methoxymethyl)-5,6-dihydropyridine-1 (2H)-carboxylate2회

생성물 1

HCID 89851925(3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide수율 100.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(dimethylcarbamoyl)-2-(methoxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 140, 1.642 g, 2.96 mmol) in DCM (8 mL) was added trifluoroacetic acid (4.33 mL, 56.25 mmol) and stirred at rt for 30 minutes. Upon addition, the color of the solution immediately turned pink. Then the solvents were evaporated and the crude product redissolved in DCM and washed with 0.5N NaOH, brine, filtered and concentrated to obtain the desired product (1.346 g, 100%) as a beige foam.

후처리

  1. additionUpon addition
  2. customThen the solvents were evaporated
  3. dissolutionthe crude product redissolved in DCM
  4. washwashed with 0.5N NaOH, brine
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e066778b96a2463ca84a14b48d3deb51
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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