反应 #1885063

ord-245117e4a2324fe4b9dadbccc2581d75

反应方程式

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
收率 81.3%

反应物

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

试剂

无

溶剂

COCCOC
DME
C1CCOC1
THF
O
H2O

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    萃取it is extracted into tert-BuOH/CHCl3/H2O
  2. 2
    其他The organic phase is separated
  3. 3
    其他dried
  4. 4
    浓缩concentrated under reduced pressure
  5. 5
    其他The residue is triturated with diethyl ether

实验过程

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.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08343928B2uspto-grants-2013_01