Reaction #534160

Reaction equation

40

4-(2-Amino-2-cyclohexyl-acetyl)-3-phenylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

HATU

DIPEA

Boc-N(Me)Ala-OH

→

41

Yield 88.0%

4-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-3-phenylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Yield 88.0%

Solvents

Et2O

NMP

Conditions

Workup

1. 1
   Washwashed with H2O, 1M HCl, H2O, saturated aqueous NaHCO3, brine
2. 2
   Dryingdried over anhydrous Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated

Procedure

A solution of Boc-N(Me)Ala-OH (155 mg, 0.76 mmol) in NMP (5 mL) was cooled to 0° C. and treated with HATU (290 mg, 0.76 mmol) and DIPEA (0.15 mL, 0.87 mmol) followed in 15 min by the addition of 40 (366 mg, 0.73 mmol). The reaction mixture was allowed to warm to ambient temperature. After 18 h, the solution was diluted with Et2O, washed with H2O, 1M HCl, H2O, saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 41 (443 mg) as a white foam that was used without further purification. Mass spectrum, m/z [690.8] (M+H)+.

Source