反応 #1885063

ord-245117e4a2324fe4b9dadbccc2581d75

反応方程式

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
収率 81.3%

反応物

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

試薬

なし

溶媒

COCCOC
DME
C1CCOC1
THF
O
H2O

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

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.

出典

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