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Trifluoroacetic acid → HCID 86664822, 화합물

HRID 1628242
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HRID 1628242 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:12]=[C:11]([NH:13][C:14](=[O:31])[C@@H:15]([NH:23]C(=O)OC(C)(C)C)[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:10]([CH3:32])[N:9]=2)[CH:5]=[CH:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:23][C@@H:15]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]([NH:13][C:11]1[N:10]([CH3:32])[N:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)[CH:12]=1)=[O:31]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86664823HCID 86664823, 화합물

생성물 1

HCID 86664822HCID 86664822, 화합물수율 58.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a 250 ml flask was added 18.8 g of tert-butyl (S)-1-(3-(2-chloropyridin-4-yl)-1-methyl-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 1.D, 100 ml of DCM and 50 ml of TFA. The reaction was stirred at room temperature for 4 hours at which time the solvent was removed with a stream of nitrogen. The crude was partitioned between 2000 ml of DCM and 500 ml of saturated aqueous sodium bicarbonate. The organic layer was extracted twice more with 500 ml of water, dried over sodium sulfate and the organic solvent was removed by rotary evaporation. The crude was purified using a silica gel column (eluting with 5% MeOH in DCM) to give 8.6 g of (2S)-2-amino-N-(3-(2-chloropyridin-4-yl)-1-methyl-1H-pyrazol-5-yl)-3-phenylpropanamide 17.7.E as a light brown solid.

후처리

  1. customwas removed with a stream of nitrogen
  2. customThe crude was partitioned between 2000 ml of DCM and 500 ml of saturated aqueous sodium bicarbonate
  3. extractionThe organic layer was extracted twice more with 500 ml of water
  4. dry with materialdried over sodium sulfate
  5. customthe organic solvent was removed by rotary evaporation
  6. customThe crude was purified
  7. washa silica gel column (eluting with 5% MeOH in DCM)

출처 및 근거

ORD 기록
ord-e988161521014d379fc78d7d2042c4d9
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785468B2

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