2-Aminopropanol → 2-(N-Hexadecanoyl)amino-1-propanol
Reaction equation
[CH3:1][CH:2]([NH2:5])[CH2:3][OH:4].[C:6](Cl)(=[O:22])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>C(Cl)Cl>[C:6]([NH:5][CH:2]([CH3:1])[CH2:3][OH:4])(=[O:22])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4.00 g (53.2 mmol) of commercially obtained dl-2-amino-1-propanol b and 8.0 g (8.8 ml, 29.3 mmol) of hexadecanoyl chloride in 100 ml of CH2Cl2 was stirred at room temperature for hours. The solution was concentrated and the residue was boiled with 200 ml acetone and decanted. The solution was concentrated and the residue was chromatographed on silica gel using 50% ethylacetate in hexane to afford 4.15 g (51%) of the title compound as white needles, m.p. 75-76° C. Using the same procedure as in Example 19, the following compounds were prepared: