Methanesulfonyl chloride → 2-(Tert-butoxycarbonyl(prop-2-ynyl)amino)ethyl methanesulfonate

HRID 1971674Notes

Reaction equation

HRID 1971674 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:12][C:13]#[CH:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(N(CC)CC)C.CCOCC>[CH3:15][S:16]([O:1][CH2:2][CH2:3][N:4]([C:5]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:11])[CH2:12][C:13]#[CH:14])(=[O:18])=[O:17]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11672867tert-Butyl (2-hydroxyethyl)(prop-2-yn-1-yl)carbamate

Product 1

HCID 581248922-(Tert-butoxycarbonyl(prop-2-ynyl)amino)ethyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 700 mg of 10d in 1 ml of triethyl amine and 15 ml of ether was treated at 0° C. with 320 μl of methanesulfonyl chloride in 3 ml of ether. The reaction mixture was stirred for ½ h and then quenched by addition of 20 ml of water and the product was extracted into ether. The organic extract was washed with 1M aq. K2CO3 and once with water, dried and concentrated, to give 900 mg of 10e as a colorless oil, essentially pure according to TLC and NMR, which was used without further purification in the next step. Rf 0.40 (heptane/ethyl acetate 1/1).

Workup

  1. customquenched by addition of 20 ml of water
  2. extractionthe product was extracted into ether
  3. extractionThe organic extract
  4. washwas washed with 1M aq. K2CO3 and once with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-15c7c6bf6316462bb235325e681b047c
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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