Reaction #309688

Reaction equation

Boc-N-methyl-L-alanine

HOBt

HBTU

(S)-2-amino-2-cyclohexyl-1-[(S)-2-(3-phenoxy-phenyl)-pyrrolidin-1-yl]-ethanone

DIPEA

→

((S) 1-{(S)-1-cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolodin-1-yl]-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester

Yield 84.0%

Solvents

brine

DMF

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (3×10 mL)
2. 2
   Dryingdried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated under reduced pressures
5. 5
   Otherpurified by silica gel column chromatography (50% EtOAc/Hexanes)

Procedure

To a solution of Boc-N-methyl-L-alanine (771 mgs, 3.79 mmol), HOBt (700 mgs, 5.17 mmol), and HBTU (2.0 g, 5.17 mmol) in DMF (10 mL) is added (S)-2-amino-2-cyclohexyl-1-[(S)-2-(3-phenoxy-phenyl)-pyrrolidin-1-yl]-ethanone and DIPEA (3 mL, 17.25 mmol). The mixture is stirred for 30 minutes and diluted with brine (20 mL) and extracted with EtOAc (3×10 mL). The organics were combined, dried over Na2SO4, filtered, concentrated under reduced pressures and purified by silica gel column chromatography (50% EtOAc/Hexanes) to give the product ((S) 1-{(S)-1-cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolodin-1-yl]-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester as a white powder (1.3 g, 84%). LCMS m/z 564 (M+1).

Source