Chlorosuccinimide → methyl 4-methyl-1,2-thiazole-3-carboxylate
Reaction equation
[CH3:1][C:2]1[CH2:9][S:8]C2[N:4](C(=O)C2NC(=O)CC2C=CC=CC=2)[C:3]=1[C:21]([O:23][CH3:24])=[O:22].C1C(=O)N(Cl)C(=O)C1>ClCCl.C(O)(C(F)(F)F)=O>[CH3:1][C:2]1[C:3]([C:21]([O:23][CH3:24])=[O:22])=[N:4][S:8][CH:9]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Methyl 3-methyl-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (I127) (971 mg, 2.80 mmol) was dissolved in dry dichloromethane (DCM) (37 mL), treated with NCS (749 mg, 5.61 mmol) before adding 2 drops of TFA (0.05 mL, 0.649 mmol) and stirring at RT for 80 mins. LCMS as run and the desired product seen. Reaction left to stand for 16 hours before work up by diluting with DCM (20 ml), washing with saturated sodium bicarbonate solution (50 ml), then water (40 ml), dried over Na2SO4 before filtering and evaporating to afford an oil. Purified on a 100 g SNAP cartridge eluting with chloroform over 10 CV. 2 spots were isolated, desired product identified and solvent evaporated to afford an orange yellow gum of desired material in 57 mg.
Sources & evidence
- ORD record
- ord-22e92d149dc449689893967807d4d8a3
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501946B2
Reaction notes
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