Methanol → Methyl 2-(S)-[N-carbobenzyloxy]amino-3-aminopropionate, hydrochloride

反応式

[NH2:1][CH2:2][C@H:3]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:4]([OH:6])=[O:5].O=S(Cl)[Cl:20].[CH3:22]O>>[ClH:20].[NH2:1][CH2:2][C@H:3]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:4]([O:6][CH3:22])=[O:5]

参加物

反応物 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 2756313Z-Dap-OH

生成物 1

HCID 13756825Methyl 2-(S)-[N-carbobenzyloxy]amino-3-aminopropionate, hydrochloride

実験手順

3-Amino-2(S)-benzyloxycarbonylaminopropionic acid (Fluka) (5.0 g, 21.0 mmoles) was suspended in MeOH and at -10° SOCl2 (23.0 mmoles) was added. The reaction mixture was allowed to gradually warm to room temperature over 16 hours. The solvent was then removed and the resulting solid was triturated with Et2O to give 10-10.