4-Methylmorpholine → (1,1-dimethylethyl) (S)-[1-methyl-2-[(2-methyl-2-propenyl)amino]-2-oxoethyl]carbamate

Reaction equation

[CH3:1][C:2]([CH3:13])([O:4][C:5]([NH:7][C@H:8]([C:10]([OH:12])=O)[CH3:9])=[O:6])[CH3:3].Cl.[CH3:15][C:16](=[CH2:19])[CH2:17][NH2:18].CN1CCOCC1>>[CH3:9][C@H:8]([NH:7][C:5](=[O:6])[O:4][C:2]([CH3:1])([CH3:3])[CH3:13])[C:10]([NH:18][CH2:17][C:16]([CH3:19])=[CH2:15])=[O:12]

Participants

Reactant 3

HCID 79724-Methylmorpholine

HCID 85082Tert-butoxycarbonylalanine

HCID 119537722-Methylallylamine hydrochloride

Product 1

HCID 53642955(1,1-dimethylethyl) (S)-[1-methyl-2-[(2-methyl-2-propenyl)amino]-2-oxoethyl]carbamateYield 99.9%

Procedure

To a cooled (0° C.) mixture of 18.9 parts of (S)-N-[(1,1,-dimethylethoxy)carbonyl]-alanine, 10.8 parts of 2-methyl-2-propen-1-amine monohydrochloride, 27.0 parts of 1-hydroxy-1H-benzotriazle hydrate and tetaahydrofuran, there were added 10.1 parts of N-methylmorpholine and, after 20 min, 20.6 parts of N,N-methanetetraylbis-[cyclohexanamine] under a nitrogen atmosphere. The whole was kept at 0° C. for 1 hour and at room temperature for 12 hours. The solvent was evaporated and the residue was partitioned between dichloromethane and NaHCO3 (sat.). The organic layer was separated, washed with NaCl (sat), dried, filtered and evaporated, yielding 24.2 parts (99.9%) of (1,1-dimethylethyl) (S)-[1-methyl-2-[(2-methyl-2-propenyl)amino]-2-oxoethyl]carbamate (interm. 63).