Chlorosulfonyl isocyanate → Carbamic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester

1.04 ml of chlorosulfonyl isocyanate (12 mmol) was slowly added to [3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methanol (2.813 g, 10 mmol) in THF (50 ml, 0.2 M) in a 250 ml-flask at −78° C. The consumption of all the starting materials was confirmed by liquid chromatography, and then water was added to the reaction mixture. After 1 hour, the THF was distilled off under reduced pressure, and the resulting solid after addition of 100 ml of water to the mixture was filtered off. The filtered solid was each washed with 100 ml of water and a solution of ethyl acetate/hexane (1/2) and then dried to obtain 3.4 g of a crude product (95.9% pure). The crude compound was recrystallized from an ethyl acetate/hexane/methylene chloride (1/4/1) solution containing 1% MeOH to obtain 2.743 g of carbamic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester of 99% purity.

1. customThe consumption of all the starting materials
2. additionwater was added to the reaction mixture
3. distillationthe THF was distilled off under reduced pressure
4. additionthe resulting solid after addition of 100 ml of water to the mixture
5. filtrationwas filtered off
6. washeach washed with 100 ml of water
7. dry with materiala solution of ethyl acetate/hexane (1/2) and then dried
8. customto obtain 3.4 g of a crude product (95.9% pure)
9. customThe crude compound was recrystallized from an ethyl acetate/hexane/methylene chloride (1/4/1) solution
10. additioncontaining 1% MeOH

ORD record

ord-5515599f81744baf815577668a4603de

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828992B2