Benzyl Alcohol → 2-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid methyl ester

Participants

Reaction Steps

To a stirred solution of 5.77 ml (66.78 mmol) of chlorosulfonyl isocyanate in methylene chloride was added, under nitrogen, phenylmethanol (6.89 ml, 66.57 mmol) at 0°-5° C. After stirring the above solution for 1 hour, a solution of 13.166 g (62.78 mmol) of 2-(3-methylbutyl)sarcosine methyl ester hydrochloride in methylene chloride containing triethylamine (27.33 ml, 194.62 mmol) was added at 0°-5° C., and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 600 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride and the combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo to yield 21.22 g (87.2%) of N-(carbobenzylxaminosulfonyl)-2-(3-methylbutyl)-sarcosine methyl ester (Formula XII: R=CH3 ; R1 =(CH2)2CH(CH3)2 ; R2 =H; R3 =CH3) which was purified by silica column chromatography (20% ethyl acetate in hexane) to afford an oil.

Provenance & Evidence