Tetrabutylammonium Fluoride → HCID 59118110, compound

Participants

Reaction Steps

To a solution of methyl 4-{(2R)-2-[((tert-butoxycarbonyl){(2R)-2-{[tert-butyl(dimethyl)silyl]-oxy}-2-[6-(2,5-dimethyl-1H-pyrrol-1-yl)-3-pyridinyl]ethyl}-amino)methyl]-3,4-dihydro-2H-chromen-6-yl}benzoate (Example 371, 213 mg, 0.29 mmol) in THF (5 mL) was added a solution of 1 M tetrabutylammonium fluoride (0.59 mL, 0.59 mmol). The mixture was stirred at room temperature for 16 hours and then concentrated in vacuo. Flash chromatography of the residue over silica gel using 40% ethyl acetate/hexanes afforded 213 mg (92%) of the desired product. The product had: 1H NMR (CDCl3δ): 8.62 (s, 1 H), 8.06 (d, J=8.9 Hz, 2 H), 7.92 (d, J=7.2 Hz, 1 H), 7.58 (d, J=8.8 Hz, 2 H), 7.31-7.40 (m, 2 H), 7.22 (d, J=7.8 Hz, 1 H), 6.89 (d, J=7.9 Hz, 1 H), 5.89 (s, 2 H), 5.10-5.26 (m, 2 H), 4.21-4.50 (m, 1 H), 3.93 (s, 3 H), 3.56-3.88 (m, 4 H), 3.15-3.42 (m, 1 H), 2.78-3.04 (m, 2 H), 2.12 (s, 6 H), 1.65-1.83 (m, 2 H), 1.50 (s, 9 H).

Provenance & Evidence