Triethylamine → 3-((Tert-butoxycarbonyl)amino)propyl methanesulfonate

HRID 1677003Notes

Reaction equation

HRID 1677003 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl.CCOC(C)=O>[CH3:20][S:21]([O:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([O:7][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:12])(=[O:23])=[O:22]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 114141093-((Tert-butoxycarbonyl)amino)propyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of tert-butyl 3-hydroxypropylcarbamate (431 mg) at 0° C. in dichloromethane, triethylamine (686 μL) was added, followed by methanesulfonyl chloride (209 μL). The reaction was stirred for 15 minutes, then allowed to warm to room temperature and stir for 1 hour more. Additional triethylamine (686 μL) and methanesulfonyl chloride (209 μL) were added. One hour later the reaction was diluted with EtOAc and washed with saturated NaHCO3 and brine. The solution was dried over Na2SO4 and concentrated in vacuo to give the titled compound. ESI+ MS: 259 [M+H]+.

Workup

  1. stirringstir for 1 hour more
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialThe solution was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c37bbe628e314dd88aa0d711323e322b
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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