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Trifluoroacetic acid → HCID 76034997、化合物

HRID 84190
ノート
印刷プレビュー

反応式

HRID 84190 の反応式
[NH2:1][O:2]C1CCCCO1.[C:9]1([S:15]([N:18]2[C:26]3[C:21](=[CH:22][C:23]([CH:27]=[CH:28][C:29]([OH:31])=O)=[CH:24][CH:25]=3)[CH2:20][CH2:19]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.C(O)(C(F)(F)F)=O>CN(C=O)C.CO>[C:9]1([S:15]([N:18]2[C:26]3[C:21](=[CH:22][C:23]([CH:27]=[CH:28][C:29]([NH:1][OH:2])=[O:31])=[CH:24][CH:25]=3)[CH2:20][CH2:19]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2724699PyBOPHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 674346323-[1-(Phenylsulfonyl)indolin-5-yl]acrylic Acid

生成物 1

HCID 76034997HCID 76034997、化合物収率 94.2%

試薬・触媒・溶媒

2
HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

NH2OTHP (0.05 g, 0.44 mmol) was added to a solution of 15 (0.12 g, 0.37 mmol), PyBOP (0.20 g, 0.39 mmol), triethylamine (0.12 ml, 0.88 mmol) in DMF (1.5 mL). The reaction mixture was stirred at room temperature for 1 h before it was quenched with water, followed by extraction with EtOAc (15 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (CH2Cl2:CH3OH=30:1:1% NH3(aq)) to give a white solid, which was treated with TFA (1.13 ml, 15.21 mmol) in the presence of CH3OH (25 mL) and stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure to give a white residue, which was recrystallized by CH3OH to afford Compound 12 (0.12 g). 1H NMR (500 MHz, CD3OD): δ 2.91 (t, J=8.5 Hz, 2H), 3.96 (t, J=8.4 Hz, 2H), 6.32 (d, J=15.8 Hz, 1H), 7.32 (s, 1H), 7.37-7.39 (m, 1H), 7.46 (d, J=15.7 Hz, 1H), 7.50-7.53 (m, 2H), 7.58-7.64 (m, 2H), 7.82 (d, J=7.8 Hz, 2H). MS (EI) m/z: 170 (100%), 344 (M+, 3.21%). HRMS (EI) for C17H16N2O4S (M+): calcd, 344.0831. found, 344.0829.

後処理

  1. customwas quenched with water
  2. extractionfollowed by extraction with EtOAc (15 mL×3)
  3. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (CH2Cl2:CH3OH=30:1:1% NH3(aq))
  6. customto give a white solid, which
  7. stirringstirred overnight at room temperature
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. customto give a white residue, which
  10. customwas recrystallized by CH3OH

出典と根拠

ORDレコード
ord-f99a4abfd9ce480db3298bfa5a4700ac
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846748B2

反応ノート

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