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.[CH3:23][O:24][C:25](=[O:30])[C@@H:26]([NH2:29])[CH2:27][OH:28]>C(Cl)Cl.CN(C=O)C.O>[OH:28][CH2:27][C@H:26]([NH:29][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:24][CH3:23])=[O:30]Participants
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. The resultant reaction mixture was stirred at RT for 1 h. The reaction mixture was diluted with DCM (200 mL) and water (25 mL) and was washed with 2N HCl (20 mL) and brine (10 mL). The separated organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained crude material was purified by silica gel column chromatography eluting with 20% EtOAc/Hexane to afford compound 3 (2.3 g) as solid.
Workup
- additionwere added drop wise at −15° C
- customThe resultant reaction mixture
- stirringwas stirred at RT for 1 h
- washwas washed with 2N HCl (20 mL) and brine (10 mL)
- dry with materialThe separated organic layer was dried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customThe obtained crude material
- customwas purified by silica gel column chromatography
- washeluting with 20% EtOAc/Hexane
Sources & evidence
- ORD record
- ord-b8b3d1717e7e4077b9380808e7bcfb84
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673843B2
Reaction notes
Loading…