4-Methylmorpholine → HCID 131719549, compound
Reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([OH:20])=O)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[NH2:28][C@H:29]([C:33]([O:35][CH3:36])=[O:34])[C@@H:30]([CH3:32])[OH:31].Cl.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C1COCC1>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([NH:28][C@H:29]([C:33]([O:35][CH3:36])=[O:34])[C@@H:30]([CH3:32])[OH:31])=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
1.14 g (3 mmol) of Boc-Lys(Z)-OH, 0.51 g (3 mmol) of H-Thr-OMe.HCl, 0.68 g of (3.6 mmol) of EDCI, 0.58 g (3.6 mmol) of HOBT and 0.66 ml (6 mmol) of NMM are dissolved at -10° C. in 10 ml THF and stirred at room temperature for 15 hours. The THF is distilled off under vacuum, the residue dissolved in 50 ml ethyl acetate and the organic phase washed three times with 10 ml 0.5 N HCl, 10% NaHCO3 solution and water respectively. The organic phase is dried with MgSO4 and the solvent distilled off under vacuum. 1.36 g (92%) of thin-layer chromatographically identical Boc-Lys(Z)-Thr-OMe are obtained as a colourless foam.
Workup
- distillationThe THF is distilled off under vacuum
- dissolutionthe residue dissolved in 50 ml ethyl acetate
- washthe organic phase washed three times with 10 ml 0.5 N HCl, 10% NaHCO3 solution and water respectively
- dry with materialThe organic phase is dried with MgSO4
- distillationthe solvent distilled off under vacuum
Sources & evidence
- ORD record
- ord-03ea1b7bed0d435d86e873c15d076124
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05556836
Reaction notes
Loading…