Methyl chloroformate → HCID 89533800, compound

Participants

Reaction Steps

To a vial was added a single enantiomer (R or S) of 3-((7-amino-5,6,7,8-tetrahydronaphthalen-1-yl)methyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (20-4) (19 mg, 0.037 mmol), then NMP (0.6 ml), DIPEA (30 μL, 0.172 mmol), and finally METHYL CHLOROFORMATE (12.30 μL, 0.159 mmol). The reaction mixture was then capped (not under N2) & stirred at room temperature. Followed by LC/MS. After 10 min at room temperature the reaction mixture was diluted with MeOH/drops of H2O/DMSO, then purified (without workup) by reverse phase chromatography (5-95% MeCN/H2O; 0.1% TFA in AQ; 20 min gradient; Waters 30×150 mm Sunfire 5 micron C18 column); desired fractions concentrated (GENEVAC), then dissolved in MeOH/DCM & concentrated to yield methyl (8-((6-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-5-fluoro-2-oxobenzo[d]oxazol-3(2H)-yl)methyl)-1,2,3,4-tetrahydronaphthalen-2-yl)carbamate (23-1). HRMS [M+H] calculated; 534.0912, observed; 534.0918. 1H NMR (499 MHz, DMSO): δ 8.48 (s, 1H); 7.79 (d, J=5.5 Hz, 1H); 7.33-7.23 (m, 2H); 7.08-7.03 (m, 2H); 6.88-6.82 (m, 1H); 5.75 (s, 1H); 5.03-4.91 (m, 2H); 3.81-3.71 (m, 2H); 3.55 (s, 3H); 3.06-2.99 (m, 1H); 2.87-2.80 (m, 2H); 1.95-1.88 (m, 1H); 1.68-1.57 (m, 1H).

Provenance & Evidence