Reaction equation
N#N.[OH:3][CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10](=[O:12])[CH3:11])[N:9]=1.CCN(CC)CC.[S:20](Cl)([CH3:23])(=[O:22])=[O:21]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:10]([C:8]1[N:9]=[C:5]([CH2:4][O:3][S:20]([CH3:23])(=[O:22])=[O:21])[O:6][CH:7]=1)(=[O:12])[CH3:11]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(2-hydroxymethyl-oxazol-4-yl)-ethanone (75 mg, 0.53 mmol) in dry CH2Cl2 (5.0 mL) was treated at 0° C. with Et3N (0.10 mL, 0.71 mmol) followed by DMAP (6 mg, 0.05 mmol) and Ms-Cl (0.05 mL, 0.66 mmol). After stirring at 0° C. for 30 min, the reaction mixture was quenched with water (10 mL), extracted with CH2Cl2 (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. TLC: rf (EA)=0.63. LC-MS-conditions 02: tR=0.64 min; [M+H]+=220.22.
Workup
- customthe reaction mixture was quenched with water (10 mL)
- extractionextracted with CH2Cl2 (10 mL)
- dry with materialextracts were dried over Na2SO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
Sources & evidence
- ORD record
- ord-d2d5547a0c8f41fea2128d6ef536ff01
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580831B2
Linked notes
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