Hydrochloric Acid → HCID 68556009, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-{4-[(3aR*,7S*,7aS*)-3-(3-tert-butyl-benzyl)-2,5,5-trioxo-octahydro-1-oxa-5lambda*6*-thia-3-aza-inden-7-ylmethyl]-2-fluoro-phenyl}-2-dimethylamino-acetamide (example 6a), 0.055 g, 0.1 mmol) in THF (1.1 mL) was added borane THF-complex (1M in THF, 1 mL, 1 mmol) at 25° C. The mixture was stirred for 17 h at 25° C. and afterwards 3 h at reflux. The reaction mixture was evaporated and diluted with EtOAc; ice cold aq. H2SO4 was added carefully and the organic layer was washed with water, brine, dried over Na2SO4, filtered and evaporated to leave an amorphous powder which was dissolved in MeOH (3 mL). and 2N aq. HCl (2.5 mL) and the solution was kept at 80° C. for 17 h. The colorless solution was basified with aq. NaOH and extracted with EtOAc. Organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give the title compound as a slight brownish foam: TLC (toluene-ETA 85:15) Rf=0.30; HPLC RtA=1.91 min; ESIMS [M+H]+=532; 1H NMR (600 MHz, DMSO-d6): δ 7.39 (s, 1H), 7.33 (m, 1H), 7.28 (t, 1H), 7.13 (d, 1H), 6.9 (d, 1H), 6.82 (d, 1H), 6.72 (t, 1H), 5.51 (d, 1H), 4.40 (d, 1H), 4.22 (d, 1H), 4.11 (t, 1H), 3.67 m, 2H), 3.44 (m, 3H), 3.01 (m, 2H), 2.84 (m, 3H), 2.55 (s, 6H), 2.46 (m, 2H), 1.25 (s, 9H).

Provenance & Evidence