Chlorosuccinimide → HCID 141627790, compound
Reaction equation
[OH:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:15][O:14][CH2:13][CH2:12][N:11]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:6][CH:5]=1.[Cl:23]N1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O.O>[Cl:23]/[C:3](/[C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[CH2:15][O:14][CH2:13][CH2:12][N:11]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:8][CH:9]=1)=[N:2]\[OH:1]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 55 °C
Procedure
To a solution of tert-butyl (3R)-3-[4-[hydroxyiminomethyl]phenyl]morpholine-4-carboxylate 12 (5.57 g, 18.18 mmol) in DMF (33.06 mL) at 55° C. was added 1-chloropyrrolidine-2,5-dione (2.549 g, 19.09 mmol) and the resulting mixture heated at 55° C. for 20 mins. The reaction mixture was then cooled to rt and diluted with EtOAc (50 mL) and water (50 mL) and the organic layer separated. The aqueous later was extracted further with extracted with EtOAc (2×50 mL) and the combined organic extracts were washed with water (3×50 mL) and brine (1×50 mL), dried over MgSO4, filtered and concentrated in vacuo to leave the product as a white foam (5.78 g, 89% yield); 1H NMR (400.0 MHz, DMSO) d 1.23 (9H, s), 3.37 (1H, m), 3.48 (1H, m), 3.75 (3H, m), 4.26 (1H, m), 5.01 (1H, s), 7.43 (2H, m), 7.78 (2H, m) and 12.40 (1H, s) ppm
Workup
- temperatureThe reaction mixture was then cooled to rt
- customthe organic layer separated
- extractionThe aqueous later was extracted further
- extractionwith extracted with EtOAc (2×50 mL)
- washthe combined organic extracts were washed with water (3×50 mL) and brine (1×50 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c0bcca4cae8245d2bec46e41f85b802a
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765751B2
Reaction notes
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