Sodium Hydroxide → HCID 19039984, compound

Participants

Reaction Steps

A mixture of 439 mg (1.06 mmol) of the product of Example 30 in 8 mL 48% HBr and 8 mL acetic acid was heated to reflux for 75 minutes under N2. The reaction mixture was cooled to room temperature, diluted with 300 mL H2O, pH adjusted to 3-4 using 2N NaOH, and extracted with twice with 150 mL ethyl acetate. The ethyl acetate extracts were combined and washed once with brine and then dried over Na2SO4. Filtration, concentration and drying yielded 0.42 g of tan solid, which was purified by silica gel chromatography (4% methanol-CH2Cl2) to yield 357 mg of pure product, an off-white powder. (84% yield) m.p.: 191°-194° C.; MS (LSIMS): 400 M+H, Base; 1H NMR (AC 300, dimethylsulfoxide-d6): δ9.58 (br s, 1H, phenol OH); IR (cm31 1): 3330, 3280, 1670. Analysis calculated: C 54.13, H 4.04, N 3.51%; C 53.99, H 3.95, N 3.49%.

Provenance & Evidence