4-Methylmorpholine → HCID 71249981, compound
Reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]([OH:18])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.[NH2:26][C@@H:27]([C@H:32]([OH:34])[CH3:33])[C:28]([O:30][CH3:31])=[O:29]>C(Cl)Cl.CN(C=O)C>[OH:34][C@H:32]([CH3:33])[C@H:27]([NH:26][C:16]([C@@H:12]1[CH2:13][CH2:14][CH2:15][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:18])[C:28]([O:30][CH3:31])=[O:29]Participants
6
Conditions
- Temperature
- -15 °C
Procedure
Compound 8 (5.0 g, 20.08 mmol) was dissolved in CH2Cl2 (50 mL), NMM (2.43 mL, 22.08 mmol) and IBCF (2.74 mL, 23.09 mmol) were added and stirred at −15° C. for 30 minutes under inert atmosphere. A mixture of (2S,3R)-methyl 2-amino-3-hydroxybutanoate (2.93 g, 22.08 mmol) and NMM (2.43 mL, 22.08 mmol) in DMF (15 mL) were added drop wise at −15° C. The resultant reaction mixture was stirred at RT for 3 h. It was diluted with DCM (200 mL) and the organic layer was washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained crude was purified by silica gel column chromatography eluting with 30% EtOAc/Hexane to afford compound 9 (3.1 g, 42%).
Workup
- additionwere added drop wise at −15° C
- customThe resultant reaction mixture
- stirringwas stirred at RT for 3 h
- washthe organic layer was washed with water (50 mL), brine (50 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customThe obtained crude
- customwas purified by silica gel column chromatography
- washeluting with 30% EtOAc/Hexane
Sources & evidence
- ORD record
- ord-3f8f29646a7c41eea55142c792c4cecf
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673843B2
Reaction notes
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