Glycine ethyl ester → (4-But-2-ynyloxy-benzenesulfonylamino)-acetic acid ethyl ester

HRID 2084841Notes

Reaction equation

HRID 2084841 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH2:5][NH2:6])[CH3:2].[CH2:8]([O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)[C:9]#[C:10][CH3:11]>C(Cl)(Cl)Cl.N1C=CC=CC=1.CCOCC>[CH2:1]([O:3][C:4](=[O:7])[CH2:5][NH:6][S:19]([C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:8][C:9]#[C:10][CH3:11])=[CH:18][CH:17]=1)(=[O:21])=[O:20])[CH3:2]

Participants

6

Reactant 2

HCID 12176Glycine ethyl esterHCID 111959284-But-2-ynyloxy-benzenesulfonyl chloride

Product 1

HCID 54356225(4-But-2-ynyloxy-benzenesulfonylamino)-acetic acid ethyl esterYield 43%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 1.00 g (7.163 mmol) of glycine ethyl ester in 10 mL of chloroform and 2.0 mL of pyridine was added 1.75 g (7.163 mmol) of 4-but-2-ynyloxy-benzenesulfonyl chloride and the reaction was stirred at room temperature for 15 h. The reaction mixture was then diluted with ether and the organics were washed with 5% HCl solution and water, dried over MgSO4, filtered and concentrated in vacuo. The resulting brown solid was washed with ether to provide 0.96 g (43%) of the sulfonamide as a white solid. Electrospray Mass Spec 311.8 (M+H)+.

Workup

  1. washthe organics were washed with 5% HCl solution and water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe resulting brown solid was washed with ether

Sources & evidence

ORD record
ord-c73394c2a86c4071a0e12b0299dfe046
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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