Sarcosine → 2-{N-Methyl[2-methyl-1-(2-methylpropanoyloxy)propoxy]carbonylamino}acetic Acid
Reaction equation
[NH:1]([CH2:3][C:4]([OH:6])=[O:5])[CH3:2].[CH3:7][CH:8]([CH3:27])[C:9]([O:11][CH:12]([O:16][C:17](ON1C(=O)CCC1=O)=[O:18])[CH:13]([CH3:15])[CH3:14])=[O:10]>>[CH3:2][N:1]([C:17]([O:16][CH:12]([O:11][C:9](=[O:10])[CH:8]([CH3:27])[CH3:7])[CH:13]([CH3:15])[CH3:14])=[O:18])[CH2:3][C:4]([OH:6])=[O:5]Participants
3
Procedure
Following the general procedure for the synthesis of acyloxyalkyl carbamates, sarcosine (0.108 g, 1.19 mmol) and 1-(2,5-dioxoazolidinyloxycarbonyloxy)-2-methylpropyl 2-methylpropanoate (0.3 g, 0.99 mmol) were reacted to provide 0.152 g (55% yield) of the title compound (37) as a colorless liquid after work-up and mass-guided preparative HPLC purification. 1H NMR (CD3OD, 400 MHz): δ=6.57 (dd, 1H), 4.19 (m, 2H), 3.03 (2s, 3H), 2.6 (m, 1H), 2.01 (br m, 1H), 1.18 (m, 6H), 1.0-0.98 (2m, 6H). MS (ESI) m/z 298.14 (M+Na)+, 274.13 (M−H)−.