Triethylamine → N-(azetidin-3-yl)methanesulfonamide

HRID 2221016Notes

Reaction equation

HRID 2221016 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([NH2:12])[CH2:9]2)C=CC=CC=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[NH:8]1[CH2:11][CH:10]([NH:12][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57445463-Amino-1-(diphenylmethyl)azetidine

Product 1

HCID 59710124N-(azetidin-3-yl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(diphenylmethyl)-3-azetidinamine (synthesized according to the methods of Arimoto et. al., J. of Antibiotics 39 (9), 1243-56, 1986)(197 mg, 0.83 mmol) in dichloromethane (10 mL) was treated with excess triethylamine at 0° C. followed by methanesulfonyl chloride (71 μL, 0.91 mmol). The reaction was stirred for 30 minutes and then concentrated and purified on silica gel (0-10% methanol/dichloromethane) to provide 185 mg of the desired product as a white solid. LC/MS: M+H 317.19 at 0.31 minutes, Method D.

Workup

  1. concentrationconcentrated
  2. custompurified on silica gel (0-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-7945981b4c7447cc93fc13ba159227bf
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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