Benzyl Alcohol → HCID 54114555, compound

Participants

Reaction Steps

To a stirred solution of 7.36 ml (84.8 mmol) of chlorosulfonyl isocyanate in 180 ml of methylene chloride was added phenylmethanol (8.82 ml, 84.9 mmol) at 0° C. over a period of 35 minutes. After stirring the above solution for 2 hours at this temperature, a solution of 15.54 g (93.28 mmol) of L-proline methyl ester hydrochloride in 500 ml of methylene chloride containing triethylamine (35.5 ml) 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 (2×200 ml) and the combined organic layer was washed with brine, dried and concentrated in vacuo to yield 31 g of N-(carbobenzyloxyaminosulfonyl)-L-proline methyl ester (Formula XIV: R=CH3 ; R1 =H; R2 and R3 together =-(CH2)3 -) as an oil.

Provenance & Evidence