Phosphate → HCID 86590602, compound

Participants

Reaction Steps

To a solution of 6-[(Naphthalene-2-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid [1-(tert-butyl-dimethyl-silanyloxymethyl)-3-methanesulfonylamino-3-oxo-propyl]-amide (160 mg, 0.24 mmol) in THF (6 mL) at 0 C. is added HF in pyridine (0.3 mL). The solution is stirred at 0 C. for 1 h, poured into pH=7 phosphate buffer, and extracted with CH2Cl2. The combined organic extracts are washed with brine, dried (Na2SO4), filtered, and concentrated. The crude residue obtained is purified by flash chromatography on silica gel (CH2Cl2/MeOH) to yield 86 mg of desired product. 1H NMR (CDCl3) δ 8.34 (s, 1H), 7.91–7.79 (m, 4H), 7.49 (m, 2H), 7.09 (d, J=8.4 Hz, 1H), 5.88 (m, 2H, 5.45 (m, 1H), 4.43 (m, 1H), 4.20 (m, 2H), 3.04 (s, 3H), 3.80–1.80 (series of m, 12H).

Provenance & Evidence