Reacción #1885063

ord-245117e4a2324fe4b9dadbccc2581d75

Ecuación de reacción

CC(C)[C@@H](C(=O)ON1C(=O)CCC1=O)N(C)C(=O)OCC1c2ccccc2-c2ccccc21
Fmoc-MeVal-OSu
NC(=O)NCCC[C@H](N)C(=O)O
L-citrulline
O=C([O-])O.[Na+]
NaHCO3
→
CC(C)[C@@H](C(=O)N[C@@H](CCCNC(N)=O)C(=O)O)N(C)C(=O)OCC1c2ccccc2-c2ccccc21
Fmoc-MeVal-Cit-COOH
Rendimiento 81.3%

Reactantes

CC(C)[C@@H](C(=O)ON1C(=O)CCC1=O)N(C)C(=O)OCC1c2ccccc2-c2ccccc21
Fmoc-MeVal-OSu
NC(=O)NCCC[C@H](N)C(=O)O
L-citrulline
O=C([O-])O.[Na+]
NaHCO3

Reactivos

Ninguno

Disolventes

COCCOC
DME
C1CCOC1
THF
O
H2O

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónit is extracted into tert-BuOH/CHCl3/H2O
  2. 2
    OtroThe organic phase is separated
  3. 3
    Otrodried
  4. 4
    Concentraciónconcentrated under reduced pressure
  5. 5
    OtroThe residue is triturated with diethyl ether

Procedimiento

To a room temperature suspension of Fmoc-MeVal-OSu (2.18 g, 4.84 mmol) in DME (13 mL) and THF (6.5 mL) is added a solution of L-citrulline (0.85 g, 4.84 mmol) and NaHCO3 (0.41 g, 4.84 mmol) in H2O (13 mL). The suspension is allowed to stir at room temperature for 16 hr, then it is extracted into tert-BuOH/CHCl3/H2O and acidified to pH=2-3 with 1 M HCl. The organic phase is separated, dried and concentrated under reduced pressure. The residue is triturated with diethyl ether resulting Fmoc-MeVal-Cit-COOH (e.g., 2.01 g) which is used without further purification.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08343928B2uspto-grants-2013_01