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Trifluoroacetic acid → (2R)-2-amino-N-{6-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}butanamide

HRID 527666
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HRID 527666 반응식
[CH3:1][C:2]1([CH3:32])[CH2:6][C:5]2[C:7]([O:11][C:12]3[N:17]=[CH:16][C:15]([NH:18][C:19]([C@H:21]([NH:24]C(=O)OC(C)(C)C)[CH2:22][CH3:23])=[O:20])=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:4]=2[O:3]1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[NH2:24][C@H:21]([CH2:22][CH3:23])[C:19]([NH:18][C:15]1[CH:16]=[N:17][C:12]([O:11][C:7]2[C:5]3[CH2:6][C:2]([CH3:1])([CH3:32])[O:3][C:4]=3[CH:10]=[CH:9][CH:8]=2)=[CH:13][CH:14]=1)=[O:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86698460tert-butyl N-[(1R)-1-[[6-[(2,2-dimethyl-3H-benzofuran-4-yl)oxy]-3-pyridyl]carbamoyl]propyl]carbamate2회

생성물 1

HCID 67958761(2R)-2-amino-N-{6-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}butanamide수율 91.5%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

To a solution of tert-butyl N-[(1R)-1-[[6-[(2,2-dimethyl-3H-benzofuran-4-yl)oxy]-3-pyridyl]carbamoyl]propyl]carbamate (Intermediate 208, 14 mg, 0.032 mmol) in dry dichloromethane (1 ml) at 0° C., TFA (98 μl, 1.268 mmol) was slowly added and the reaction mixture was stirred for 4 hours at the same temperature. Some more dichloromethane (4 ml) was added to the reaction mixture. An aqueous saturated aqueous solution of NaHCO3 was then added while the pH was allowed to reach ˜8. Two phases were separated and the aqueous one was further extracted with DCM (3×3 ml). Combined organic layers were dried over Na2SO4, filtrated and evaporated affording the title compound (10 mg).

후처리

  1. customTwo phases were separated
  2. extractionthe aqueous one was further extracted with DCM (3×3 ml)
  3. dry with materialCombined organic layers were dried over Na2SO4
  4. filtrationfiltrated
  5. customevaporated

출처 및 근거

ORD 기록
ord-179f9c0fc39b40dbbc86416d69c536ed
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09346790B2

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