4-Methylmorpholine → methyl 1-[methyl(N-{[(phenylmethyl)oxy]carbonyl}glycyl)amino]cyclopropanecarboxylate
Reaction equation
[CH3:1][NH:2][C:3]1([C:6]([O:8][CH3:9])=[O:7])[CH2:5][CH2:4]1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[C:27]1([CH2:33][O:34][C:35]([NH:37][CH2:38][C:39](O)=[O:40])=[O:36])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:1][N:2]([C:39](=[O:40])[CH2:38][NH:37][C:35]([O:34][CH2:33][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:36])[C:3]1([C:6]([O:8][CH3:9])=[O:7])[CH2:5][CH2:4]1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 1-(methylamino)cyclopropanecarboxylate (1.53 g, 11.85 mmol) and HOBt (1.920 g, 14.21 mmol) in CH2Cl2 (30 mL) was added 4-methylmorpholine (5.2 mL, 47.40 mmol), N-{[(phenylmethyl)oxy]carbonyl}glycine (2.48 g, 11.85 mmol), and EDCI (2.73 g, 14.21 mmol). After stirring overnight, the solution was washed 6 N aq. HCl (100 mL) and water (100 mL). The aqueous layers were extracted with CH2Cl2 (1×100 mL), and the combined organic layers were washed with water (100 mL) and brine (100 mL), then dried over anhydrous MgSO4 and concentrated in vacuo to provide pure methyl 1-[methyl(N-{[(phenylmethyl)oxy]carbonyl}glycyl)amino]cyclopropanecarboxylate (3.66 g, 97%). LCMS: (M+H)+: 321.1.
Workup
- washthe solution was washed 6 N aq. HCl (100 mL) and water (100 mL)
- extractionThe aqueous layers were extracted with CH2Cl2 (1×100 mL)
- washthe combined organic layers were washed with water (100 mL) and brine (100 mL)
- dry with materialdried over anhydrous MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-505dbba79ad149278e7584c29a1091c0
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893056B2
Reaction notes
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