Acetic Anhydride → HCID 68185408, compound

Participants

Reaction Steps

1-Methylethyl {(2S,4R)-1-acetyl-2-methyl-6-[(2-oxopropyl)amino]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (for a preparation see Intermediate 111) (200 mg, 0.553 mmol) was dissolved in acetic anhydride (1044 μl, 11.07 mmol) and the resulting mixture was stirred at room temperature under nitrogen for 1 h then partitioned between water (2 mL) and DCM (5 mL). The layers were separated and the organic phase washed with water, dried over Na2SO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 10 to 100% AcOEt in hexanes) gave 1-methylethyl {(2S,4R)-1-acetyl-6-[acetyl(2-oxopropyl)amino]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (130 mg, 0.274 mmol, 49%) as an orange oil.

Provenance & Evidence