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

HRID 1595495

반응식

HRID 1595495 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-79a2174653aa4d7689200bc2493fb569
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288096B1

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