Reaction #534142

Reaction equation

HATU

Boc-N(Me)Ala-OH

17

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

DIPEA

→

18

Yield 115.7%

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

Yield 115.7%

Solvents

EtOAc

NMP

NMP

Conditions

Workup

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

Procedure

A solution of Boc-N(Me)Ala-OH (113 mg, 0.56 mmol) in NMP (4 mL) was cooled to 0° C. and treated with HATU (207 mg, 0.54 mmol) followed by DIPEA (0.15 mL, 0.87 mmol). After 10 min, 17 (245 mg, 0.55 mmol) in NMP (5 mL) was added. The reaction mixture was allowed to warm to ambient temperature overnight. The solution was diluted with EtOAc, washed successively with 1M HCl, saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated to afford 18 as an orange-colored oil (400 mg) which was used without further purification.

Source