Dichloromethane → D-Serine benzyl ester hydrochloride

反応式

[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]=1

参加物

反応物 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 12953536Boc-D-Ser-OBzl

生成物 1

HCID 11776084D-Serine benzyl ester hydrochloride

実験手順

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.