4-Methylmorpholine → HCID 11616671, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.[NH2:23][C@@H:24]([CH2:29][OH:30])[C:25]([O:27][CH3:28])=[O:26]>C(Cl)Cl.CN(C=O)C.O>[OH:30][CH2:29][C@H:24]([NH:23][C:13]([C@@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15])[C:25]([O:27][CH3:28])=[O:26]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -15 °C
Procedure
Compound 2 (2.0 g, 9.00 mmol) was dissolved in CH2Cl2 (10 mL) cooled to −15° C., NMM (1.12 mL, 10.2 mmol) and IBCF (1.26 mL, 1.15 mmol) were added and stirred at 0° C. for 20 minutes. A mixture of (S)-methyl 2-amino-3-hydroxypropanoate (1.59 g, 10.2 mmol) and NMM (1.12 mL) in DMF (3 mL) were added drop wise at −15° C. and the resultant reaction mixture was stirred at RT for 1 h. It was diluted with DCM (200 mL), water (50 mL) and washed with 2N HCl (20 mL) and brine (2×50 mL). The separated organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue obtained was purified by silica gel column chromatography eluting with 20% EtOAc/Hexane to afford compound 3 (2.3 g) as a syrup.
Workup
- additionwere added drop wise at −15° C.
- customthe resultant reaction mixture
- stirringwas stirred at RT for 1 h
- washwashed with 2N HCl (20 mL) and brine (2×50 mL)
- dry with materialThe separated organic layer was dried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customThe crude residue obtained
- customwas purified by silica gel column chromatography
- washeluting with 20% EtOAc/Hexane
Sources & evidence
- ORD record
- ord-580d4c821c5e4818a612627b2f754831
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673843B2
Reaction notes
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