4-Methylmorpholine → methyl (2R)-1-(N-{[(phenylmethyl)oxy]carbonyl}glycyl)-2-piperidinecarboxylate
Reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[C:8]([O:10][CH3:11])=[O:9].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[C:29]1([CH2:35][O:36][C:37]([NH:39][CH2:40][C:41](O)=[O:42])=[O:38])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:29]1([CH2:35][O:36][C:37]([NH:39][CH2:40][C:41]([N:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]2[C:8]([O:10][CH3:11])=[O:9])=[O:42])=[O:38])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl (2R)-2-piperidinecarboxylate hydrochloride (1.0 g, 5.56 mmol) and HOBt (0.90 g, 6.67 mmol) in CH2Cl2 (20 mL) was added 4-methylmorpholine (2.44 mL, 22.24 mmol), N-{[(phenylmethyl)oxy]carbonyl}glycine (1.16 g, 5.56 mmol), and EDCI (1.28 g, 6.67 mmol). After stirring overnight, the solution was washed 6 N aq. HCl (100 mL) and water (100 mL). The aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), and then dried over anhydrous MgSO4 and concentrated in vacuo to provide methyl (2R)-1-(N-{[(phenylmethyl)oxy]carbonyl}glycyl)-2-piperidinecarboxylate (2.029 g, 99%). LCMS: (M+H)+: 335.1.
Workup
- washthe solution was washed 6 N aq. HCl (100 mL) and water (100 mL)
- extractionThe aqueous layer was extracted with CH2Cl2 (3×50 mL)
- washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
- dry with materialdried over anhydrous MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-48fd90e5d0b4451a8eac6ebad9ec5691
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893056B2
Reaction notes
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