반응 #1885063

ord-245117e4a2324fe4b9dadbccc2581d75

반응 방정식

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
수율 81.3%

반응물

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

시약

없음

용매

COCCOC
DME
C1CCOC1
THF
O
H2O

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    추출it is extracted into tert-BuOH/CHCl3/H2O
  2. 2
    기타The organic phase is separated
  3. 3
    기타dried
  4. 4
    농축concentrated under reduced pressure
  5. 5
    기타The residue is triturated with diethyl ether

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08343928B2uspto-grants-2013_01