3-Nitrobenzenesulfonyl chloride → 4-(Tert-butoxycarbonylamino)phenethyl 3-nitro-benzenesulfonate

HRID 1595495

反応式

HRID 1595495 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:18]([C:21]1[CH:22]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19]>ClCCl>[N+:18]([C:21]1[CH:22]=[C:23]([S:27]([O:17][CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:14][CH:13]=2)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19]

参加物

4

反応物 2

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 11413715N-Boc-2-(4-aminophenyl)ethanol

生成物 1

HCID 545354424-(Tert-butoxycarbonylamino)phenethyl 3-nitro-benzenesulfonate収率 47%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-25 °C

実験手順

2-[4-(tert-butoxycarbonylamino)phenyl]-1-ethanol dissolved in dichloromethane. The reaction mixture was cooled to −25° C. and 9.34 g (42 mmole) 3-nitrobenzenesulfonyl chloride was added in portions. The reaction mixture was poured on to icewater, the phases were separated and the organic phase was dried (sodium sulfate), filtered and the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel using dichloromethane as eluent to give 8.3 g (yield 47%) 4-(tert-butoxycarbonylamino)-phenethyl 3-nitro-benzenesulfonate as yellow crystals.

後処理

  1. additionThe reaction mixture was poured on to icewater
  2. customthe phases were separated
  3. dry with materialthe organic phase was dried (sodium sulfate)
  4. filtrationfiltered
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-79a2174653aa4d7689200bc2493fb569
出典データセット
uspto-grants-2001_09
特許番号
US06288096B1

関連ノート

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