Hydrochloric Acid → (R)-2-(2-(1H-indol-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)acetic acid

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Reaction Conditions

Reaction Steps

A mixture of (R)-tert-butyl 2-(2-(1H-indol-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)acetate (250 mg, 0.593 mmol), HCl (4M in 1,4-dioxane) (10 mL, 40.0 mmol) and 1 N hydrochloric acid (2 mL, 2 mmol) was stirred at 70° C. for 1 hour. The mixture was subsequently concentrated in vacuo to give an HCl salt of the title compound as a brown solid (245 mg, 103%). 1H NMR (400 MHz, DMSO-d6) δ 3.17-3.74 (m, 5 H), 3.90-4.03 (m, 2 H), 4.06-4.17 (m, 2 H), 4.46 (d, J=18.19 Hz, 1 H), 4.73 (d, J=12.13 Hz, 1 H), 7.00 (br s, 1 H), 7.29 (t, J=7.83 Hz, 1 H), 7.52-7.62 (m, 2 H), 7.69 (d, J=7.83 Hz, 2 H), 11.61 (br s, 1 H), 13.14 (br s, 1 H) 14.22 (br s, 1 H). ESI-MS m/z [M+H]+ calc'd for C19H19N5O3, 366.15; found 366.2.

Provenance & Evidence