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

HRID 1595495Notes

Reaction equation

HRID 1595495 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-25 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-79a2174653aa4d7689200bc2493fb569
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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