Benzyl chloroformate → ((Benzyloxy)carbonyl)-L-allothreonine
Reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C@H:13]([C:17]([OH:19])=[O:18])[C@H:14]([CH3:16])[OH:15].C([O-])(O)=O.[Na+]>O>[C:9]([NH:12][C@H:13]([C:17]([OH:19])=[O:18])[C@H:14]([CH3:16])[OH:15])([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Benzylchloroformate (0.35 ml; 2.3 mmol) was added to a mixture of L-allothreonine (0.25 g; 2.1 mmol) and NaHCO3 (435 mg; 5.18 mmol) in 2.5 ml of H2O at RT. After 3 h, the reaction mixture was partitioned between Et2O and H2O. The aqueous layer was washed with Et20, acidified to pH <2 with 6N HCl, and extracted with CH2Cl2. The organic layer was dried (MgSO4) and concentrated to afford 320 mg (63%) of Cbz-L-allothreonine.