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

HRID 339629Notes

Reaction equation

HRID 339629 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].CCN(CC)CC.[C:13]([O:17][C:18](=[O:24])[NH:19][CH2:20][CH2:21][CH2:22][OH:23])([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl>[C:13]([O:17][C:18]([NH:19][CH2:20][CH2:21][CH2:22][O:23][S:2]([CH3:1])(=[O:4])=[O:3])=[O:24])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MsCl (6.5 mL, 84 mmol) was added slowly to a solution of Et3N (16.0 mL, 114 mmol) and (3-hydroxy-propyl)-carbamic acid tert-butyl ester (13.4 g, 76.5 mmol) in CH2Cl2 (200 mL) at 0° C. (bath temp). The reaction mixture was stirred at rt for 2 h and then quenched with H2O (100 mL). The aqueous layer was extracted with CH2Cl2 and the organic fractions were then dried (MgSO4) and concentrated in vacuo. The title compound was isolated as a colorless oil: yield 18.9 g (98%).

Workup

  1. customquenched with H2O (100 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialthe organic fractions were then dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-233687a32ed04d5ea5ce2b098b091095
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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