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Trifluoroacetic acid → (S)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione

HRID 2191223
ノート
印刷プレビュー

反応式

HRID 2191223 の反応式
[O:1]([CH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[O:28]=[C:29]1[C:37](=[O:38])[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([S:39](Cl)(=[O:41])=[O:40])[CH:35]=2)[NH:30]1>C(Cl)Cl.C1COCC1>[O:1]([CH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[S:39]([C:34]1[CH:35]=[C:36]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:28])[C:37]2=[O:38])(=[O:40])=[O:41])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6422Trifluoroacetic acidHCID 10636271(S)-tert-Butyl 2-(phenoxymethyl)pyrrolidine-1-carboxylateHCID 159089472,3-Dioxoindoline-5-sulfonyl chloride

生成物 1

HCID 9821545(S)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione収率 84.6%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
0 °C

実験手順

To a solution of 9 (1.46 g, 5.2 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (5 mL) at 0° C. The mixture was stirred at 0° C. for 15 min. After evaporation of the solvent in vacuo, CH2Cl2 (15 mL) and triethylamine (2 mL) were added, then a solution of 6 (1.44 g, 5.9 mmol) in THF (25 mL) was added at 0° C. The reaction mixture was stirred overnight at room temperature. The solvent was evaporated in vacuo, then ethyl acetate (150 mL) was added, washed with water (50 mL×2) and saturated NaCl (50 mL), and dried over Na2SO4. After evaporation of the ethyl acetate, the crude product was purified with ether to afford 1.7 g (84%) of 10 as a yellow solid, mp 204.5-205.9° C. 1H NMR (300 MHz, CDCl3) δ 8.94 (s, 1H), 7.77 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.67 (s, 1H), 7.02 (t, J=8.7 Hz, 2H), 6.84 (d, J=8.1 Hz, 1H), 6.69 (t, J=7.2 Hz, 1H), 6.63 (d, J=7.8 Hz, 2H), 3.89 (m, 1H), 3.75-3.66 (m, 2H), 3.23 (m, 1H), 2.96 (m, 1H), 1.72 (m, 2H), 1.54-1.42 (m, 2H). LRMS (FAB) m/e: 387.1 (M+H, 100). Anal. Calcd for C19.N2O5S: C, 59.06, H, 4.70; N, 7.25. Found: C, 58.99, H, 4.74, N, 7.11.

後処理

  1. customAfter evaporation of the solvent in vacuo, CH2Cl2 (15 mL) and triethylamine (2 mL)
  2. additionwere added
  3. stirringThe reaction mixture was stirred overnight at room temperature
  4. customThe solvent was evaporated in vacuo
  5. additionethyl acetate (150 mL) was added
  6. washwashed with water (50 mL×2) and saturated NaCl (50 mL)
  7. dry with materialdried over Na2SO4
  8. customAfter evaporation of the ethyl acetate
  9. customthe crude product was purified with ether

出典と根拠

ORDレコード
ord-d227becdb8df4ce79f0b3a00bea9d21e
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329686B2

反応ノート

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