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

HRID 1978393Notes

Reaction equation

HRID 1978393 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][OH:18])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:19][S:20]([O:18][CH2:17][CH2:16][CH2:15][C:12]1[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]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

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

Product 1

HCID 219936273-{4-[(Tert-butoxycarbonyl)amino]phenyl}propyl methanesulfonateYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 3-(4-tert-butoxycarbonylaminophenyl)propanol (2.66 g, 10.6 mmol), methanesulfonylchloride (1.33 g, 11.6 mmol), triethylamine (1.18 g, 11.7 mmol) and ethyl acetate (10 ml) was stirred at room temperature for 1 hour. Then the reaction mixture was diluted with ethyl acetate and successively washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (50 g) with hexane-ethyl acetate (3:1) to give 3-(4-tert-butoxycarbonylaminophenyl)propyl methanesulfonate as colorless crystals (2.75 g, 79%).

Workup

  1. washsuccessively washed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel (50 g) with hexane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-723105fe2fa64ad4a6cdbefe76dd0afd
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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