Triethylamine → HCID 9798338, compound

Participants

Reaction Steps

The deprotected material N-{[(5S)-3-(2-methyl-2,3-dihydro-1H-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide (0.48 g, 1.66 mmol) (EXAMPLE 1, Step 6) and triethylamine (0.35 mL, 2.5 mmol) are dissolved in CH2Cl2 (10 mL). Acetoxyacetylchloride (0.233 mL, 2.16 mmol) is added along with additional CH2Cl2 (25 mL). After 20 minutes the mixture is diluted with CH2Cl2 (200 mL) and washed with water, brine and dried (Na2SO4). Removal of solvent gave a residue that is dissolved in MeOH (20 mL) and CH2Cl2 (80 mL). Potassium carbonate (200 mg) is added and the reaction is stirred for 20 minutes and evaporated to dryness. The residue is purified on silica gel with 2% MeOH/CH2Cl2 to give 0.5 g (86%) of an off white solid: mp 130-133° C.; HRMS (FAB) calcd for C17H21N3O5+H1 348.1559, found 348.1569.Anal. Calcd for C17H21N3O5: C, 58.78; H, 6.09; N, 12.10.Found: C, 58.60; H, 6.27; N, 11.53.

Provenance & Evidence