Trifluoroacetic acid → (S)-N-(2-fluoro-6-(trifluoromethyl)phenyl)-1-((S)-3-methyl-2-((S)-2-(methylamino)propanamido)butanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 627044ノート

反応式

HRID 627044 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[NH:12][C:13]([C@H:15]1[N:23]([C:24](=[O:43])[C@@H:25]([NH:29][C:30](=[O:42])[C@@H:31]([N:33](C)[C:34](=O)OC(C)(C)C)[CH3:32])[CH:26]([CH3:28])[CH3:27])[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[CH2:16]1)=[O:14].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:9])([F:10])[F:11])[C:3]=1[NH:12][C:13]([C@H:15]1[N:23]([C:24](=[O:43])[C@@H:25]([NH:29][C:30](=[O:42])[C@@H:31]([NH:33][CH3:34])[CH3:32])[CH:26]([CH3:27])[CH3:28])[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[CH2:16]1)=[O:14]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 131735264tert-butyl (S)-1-((S)-1-((S)-2-(2-fluoro-6-(trifluoromethyl)phenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate

生成物 1

HCID 73603779(S)-N-(2-fluoro-6-(trifluoromethyl)phenyl)-1-((S)-3-methyl-2-((S)-2-(methylamino)propanamido)butanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide収率 59.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a 50 mL round-bottomed flask, tert-butyl (S)-1-((S)-1-((S)-2-(2-fluoro-6-(trifluoromethyl)phenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate (20 mg, 32.8 μmol Eq: 1.00) was combined with DCM (1.5 mL) to give a colorless solution. TFA (500 μL, 6.49 mmol, Eq: 198) was added and the reaction mixture was stirred at rt for 30 min. The crude reaction mixture was concentrated in vacuo. The residue was taken up in DCM, washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated in vacuo to give (S)—N-(2-fluoro-6-(trifluoromethyl)phenyl)-1-((S)-3-methyl-2-((S)-2-(methylamino)propanamido)butanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide as a white solid (10 mg), m/z=510.

後処理

  1. customto give a colorless solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-50905993abaa466e8167a55bd2ad8ee0
出典データセット
uspto-grants-2016_04
特許番号
US09309248B2

反応ノート

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