Reaction #48759

Reaction equation

hexylmethylcarbamic chloride

(2R,5R)-5-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-cyclohexylmethoxymorpholine-4-carboxylic acid tert-butyl ester

pyridine

→

3-[(1S,2S)-2-((3R,6R)-6-Cyclohexylmethoxymorpholin-3-yl)-1-(3,5-difluorobenzyl)-2-hydroxyethyl]-1-hexyl-1-methylurea hydrochloride

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherPerform purification, isolation, trifluoroacetic acid deprotection and salt exchange

Procedure

Add hexylmethylcarbamic chloride (11 mg, 0.062 mmol) to a solution of (2R,5R)-5-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-cyclohexylmethoxymorpholine-4-carboxylic acid tert-butyl ester (30 mg, 0.062 mmol) and pyridine (10 μL, 0.123 mmol) in dichloromethane at 0° C. Heat to 55° C. for four days. Perform purification, isolation, trifluoroacetic acid deprotection and salt exchange according to the procedure essentially as described for (E)-2-methyl-but-2-enoic acid [(1S,2S)-2-((3R,6R)-6-cyclohexylmethoxymorpholin-3-yl)-1-(3,5-difluorobenzyl)-2-hydroxyethyl]-amide hydrochloride.

Source