Acetic Acid → HCID 28280528, compound

Reaction equation

Cl.[S:2]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1CC#N)([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:20]([OH:23])(=[O:22])[CH3:21]>>[S:2]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[CH2:21][C:20]([OH:23])=[O:22])([C:5]1[CH:6]=[CH:7][C:8]([CH3:9])=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 313Hydrochloric Acid

HCID 57059856HCID 57059856, compound

Product 1

HCID 28280528HCID 28280528, compoundYield 48.2%

Procedure

Concentrated hydrochloric acid (20 ml) was added to a solution of (2S)-2-(1-tosylpyrrolidin-2-yl) acetonitrile (4.35 g) prepared in Reference Example 50 in acetic acid (4 ml) and then the reaction solution was heated under reflux for 3 hours. After cooling the reaction solution, it was poured into ice water and then extracted with ether. The resulting organic phase was washed with water, dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was subjected to silica gel column chromatography and then eluted with chloroform/methanol (99/1) to give 6.93 g (yield 48.2%) of the title compound.