Water → (S)-1-phenyl-1-(tert-butoxycarbonylamino)-2-(1-trifluoroacetylindoline-5-sulfonyl)aminoethane

HRID 508138ノート

反応式

HRID 508138 の反応式
[C:1]1([C@H:7]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][N:9]=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:20][C:21]([F:38])([F:37])[C:22]([N:24]1[C:32]2[C:27](=[CH:28][C:29]([S:33](Cl)(=[O:35])=[O:34])=[CH:30][CH:31]=2)[CH2:26][CH2:25]1)=[O:23].O>ClCCl.[Pd]>[C:1]1([C@H:7]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][NH:9][S:33]([C:29]2[CH:28]=[C:27]3[C:32](=[CH:31][CH:30]=2)[N:24]([C:22](=[O:23])[C:21]([F:38])([F:20])[F:37])[CH2:25][CH2:26]3)(=[O:34])=[O:35])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 962WaterHCID 110883061-(Trifluoroacetyl)-2,3-dihydro-1H-indole-5-sulfonyl chlorideHCID 86762376HCID 86762376、化合物

生成物 1

HCID 117641850(S)-1-phenyl-1-(tert-butoxycarbonylamino)-2-(1-trifluoroacetylindoline-5-sulfonyl)aminoethane

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-20 °C

実験手順

A mixture of (S)-2-phenyl-2-tert-butoxycarbonylaminoethylazide (10.50 g, 0.04 mol) dissolved in 250 mL dichloromethane and 2.5 g of 10% Pd/C was hydrogenated for 5 hrs at 70 psi of H2. The catalyst was separated by filtration. To the filtrate triethylamine (8 mL) was added, the mixture was cooled to −20° C. followed by slow addition of 1-(trifluoroacetyl)indoline-5-sulfonyl chloride (12.56 g, 0.04 mol) dissolved in 150 mL dichloromethane. The reaction mixture was then stirred overnight at room temperature. Water (500 mL) was added and the mixture was shaken well, organic layer was separated, shaken with 200 mL 2% citric acid, separated and dried with MgSO4. The drying agent was separated by filtration. The filtrate was concentrated and the title product was precipitated by addition of hexane. Yield: 17.67 g, (86%); (MH)+=514; 1H NMR (DMSO-d6): 1.33 (s, 9H), 2.85-2.99 (m, 2H), 3.26-3.30 (t, J=8.0 Hz, 2H), 4.31-4.35 (t, J=8.0 Hz, 2H), 4.53-4.59 (m, 1H), 7.19-7.35 (m, 6H), 7.66-7.68 (m, 2H), 7.72-7.75 (t, J=6.0 Hz, 1H), 8.13-8.15 (d, J=8.8 Hz, 1H).

後処理

  1. customThe catalyst was separated by filtration
  2. additionTo the filtrate triethylamine (8 mL) was added
  3. stirringthe mixture was shaken well
  4. customorganic layer was separated
  5. stirringshaken with 200 mL 2% citric acid
  6. customseparated
  7. dry with materialdried with MgSO4
  8. customThe drying agent was separated by filtration
  9. concentrationThe filtrate was concentrated
  10. customthe title product was precipitated by addition of hexane

出典と根拠

ORDレコード
ord-d3ff2208c9044d21b4420877514a093f
出典データセット
uspto-grants-2015_08
特許番号
US09095575B2

反応ノート

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