Triethylamine → 3-{4-[(Tert-butoxycarbonyl)amino]phenyl}propyl methanesulfonate

HRID 1375724Notes

Reaction equation

HRID 1375724 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:18])=[CH:7][CH:6]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 219940133-(4-Tert-butoxycarbonylaminophenyl)propanol

Product 1

HCID 219936273-{4-[(Tert-butoxycarbonyl)amino]phenyl}propyl methanesulfonateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(3-hydroxypropyl)phenylcarbamate (327 mg, 1.301 mmol) in DCM (15 ml) was cooled in an ice-bath. Triethylamine (0.23 ml, 1.626 mmol) was added, and then methanesulfonyl chloride (164 mg, 1.431 mmol) was added. The mixture was stirred overnight and the temperature was allowed going up to room temperature. It was then washed with water, sodium hydrogencarbonate aqueous solution (1%), water and brine and dried with magnesium sulfate. Evaporation in vacuum to remove the solvent gave the desired product (394 mg), yield 92%.

Workup

  1. customwas allowed going up to room temperature
  2. washIt was then washed with water, sodium hydrogencarbonate aqueous solution (1%), water and brine
  3. dry with materialdried with magnesium sulfate
  4. customEvaporation in vacuum
  5. customto remove the solvent

Sources & evidence

ORD record
ord-1e3ee5b0a1664b63aabe94ef44f9b7f0
Source dataset
uspto-grants-2007_01
Patent number
US07169810B2

Reaction notes

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