[CH:1]1([CH2:10][C:11]([OH:13])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.Cl.[CH2:26]([O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][S:33][CH2:32][NH:31]1)[CH3:27]>C(Cl)Cl>[CH2:26]([O:28][C:29](=[O:35])[C@@H:30]1[CH:34]([C:11](=[O:13])[CH2:10][CH:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)[S:33][CH2:32][NH:31]1)[CH3:27]While chilling with ice water, 1.4 g of 2-indanyl-acetic acid and 1.9 g of WSC.HCl were added to 15 ml of methylene chloride, and the mixture was stirred at room temperature for 5 minutes. Then, 1.3 g of L-thioproline ethyl ester dissolved in 10 ml of methylene chloride were added at room temperature, and the mixture was stirred further for 5 hours. The resultant liquid reaction mixture was washed with water, diluted hydrochloric acid and a saturated aqueous solution of sodium bicarbonate in that order. After an organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resultant residue was subjected to column chromatography on silica gel, thereby obtaining 1.45 g (57%) of 3-(2-indanylacetyl)-L-thioproline ethyl ester in the form of colorless oil.
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