Hydrochloric Acid → 2-(Hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acid

反応式

[Li+].[OH-:2].[CH2:3]([N:9]([CH3:20])[C:10]([CH:12]1[CH2:17][CH:16]2[CH2:18][CH:13]1[C:14](=[O:19])[O:15]2)=[O:11])[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].Cl>>[CH2:3]([N:9]([CH3:20])[C:10]([CH:12]1[CH2:17][CH:16]([OH:15])[CH2:18][CH:13]1[C:14]([OH:2])=[O:19])=[O:11])[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8]

参加物

反応物 3

HCID 313Hydrochloric Acid

HCID 3939Lithium Hydroxide

HCID 591654883-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carboxylic acid hex-5-enyl-methylamide

生成物 1

HCID 684256202-(Hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acid収率 88%

実験手順

A solution of LiOH (105 mg in 4 mL, of water) was added at 0° C. to the lactone amide (65). After 1 h, the conversion was completed (HPLC). The mixture was acidified to pH 2-3 with 1N HCl, extracted with EtOAc, dried (MgSO4), evaporated, co-evaporated with toluene several times, and dried under high vacuum overnight to give the title compound (520 mg, 88%), m/z=270 (M+H)+.