Dichloromethane → D-Serine benzyl ester hydrochloride
Reaction equation
[CH2:1]([O:8][C:9](=[O:21])[C@@H:10]([CH2:19][OH:20])[NH:11]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:30]>>[ClH:30].[CH2:1]([O:8][C:9](=[O:21])[C@@H:10]([CH2:19][OH:20])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
A solution of Boc-(D)-serine benzyl ester (1.1 g) in 1/1 mixture of the TFA and methylene chloride was stirred for 1 hour and then concentrated and azeotroped from toluene to give D-serine benzyl ester HCl salt. The residue was dissolved in methylene (15 ml), and added methyl benzimidate HCl (732 mg) and TEA (0.5 ml). The mixture was stirred at room temperature for 3 hours and then concentrated. Purification by flash chromatography (hexanes/ethyl acetate=6/1) gave 572 mg of the title compounds.