Ethyl propiolate → HCID 69055050, compound

HRID 2102485Notes

Reaction equation

HRID 2102485 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2O[C:20](=O)[S:19][N:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:27][CH2:28][CH3:29])(=[O:26])[C:24]#[CH:25]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[CH:25]=[C:24]([C:23]([O:27][CH2:28][CH3:29])=[O:26])[S:19][N:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[C:24]([C:23]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][S:19][N:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 69053852HCID 69053852, compound

Product 2

HCID 69055050HCID 69055050, compoundHCID 69058706HCID 69058706, compound

Procedure

A solution of the crude residue from example 131 and ethyl propiolate (2 mL) in xylenes (15 mL) was heated in a sealed tube at 150° C. for 4 hr. Concentration and chromatographic purification (25% ethyl acetate and hexanes) afforded 3-(5-ethoxycarbonyl-isothiazol-3-yl )-piperidine-1-carboxylic acid benzyl ester and 3-(4-ethoxycarbonyl-isothiazol-3-yl )-piperidine-1-carboxylic acid benzyl ester as a 1:1 mixture (1.24 g), MH+( LCMS) 375.1(m/z).

Workup

  1. concentrationConcentration and chromatographic purification (25% ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-551973c745d04d57bfdb12281757ecf2
Source dataset
uspto-grants-2009_08
Patent number
US07576085B2

Reaction notes

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