Trifluoroacetic acid → (3S)-3-amino-1-methyl-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-2-one

HRID 624303노트

반응식

HRID 624303 반응식
FC(F)(F)C(O)=O.[CH3:8][N:9]1[CH2:13][CH2:12][C@@:11]([NH:34]C(=O)OC(C)(C)C)([CH2:14][C:15]#[C:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:33])([F:32])[F:31])[CH:24]=3)[CH:20]=[CH:19][N:18]=2)[C:10]1=[O:42].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[NH2:34][C@@:11]1([CH2:14][C:15]#[C:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:33])([F:32])[F:31])[CH:24]=3)[CH:20]=[CH:19][N:18]=2)[CH2:12][CH2:13][N:9]([CH3:8])[C:10]1=[O:42]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 89649351tert-butyl N-[(3S)-1-methyl-2-oxo-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-3-yl]carbamate

생성물 1

HCID 89648960(3S)-3-amino-1-methyl-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-2-one수율 111.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (10 mL, 134.63 mmol) was added to a solution of the tert-butyl N-[(3S)-1-methyl-2-oxo-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-3-yl]carbamate (which may be prepared as described in Description 10) (5.38 g, 10.99 mmol) in DCM (50 mL) at 20° C. and the reaction was stirred until complete. Solid K2CO3 was added to quench the TFA present and the mixture was diluted with water. The phases were separated and the aqueous layer was washed with dichloromethane (×2). The combined organic layers were dried (MgSO4) and the solvent was evaporated to give the (3S)-3-amino-1-methyl-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-2-one (D11) (4.78 g, 12.276 mmol, 111.7% yield) as an amber oil containing some Ph3PO;

후처리

  1. customto quench the TFA present
  2. additionthe mixture was diluted with water
  3. customThe phases were separated
  4. washthe aqueous layer was washed with dichloromethane (×2)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-931e96225e4241f39bfd8af2088992f4
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303032B2

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