Methanol → HCID 10898723, compound

A solution of N-tritylimidazolylpropanol (S)-(6) (2.39 g, 6.51 mmol) in 80 ml methanol containing 4.3 ml glacial acetic acid (5%) was refluxed for about 12 hours. After that time, TLC indicated disappearance of the starting materials. The mixture was concentrated in vacuo and a white precipitate appeared upon addition of 50 ml of cold distilled water. The mixture was chilled, then filtered, and the white precipitate was washed with cold distilled water (10 ml). The filtrate was then evaporated twice, and the residual yellow oil redissolved in 50 ml dry methanol and passed through the weakly basic anion exchange resin (hydroxide form) IRA-68. The solution was then evaporated to yield a solid residue that could be recrystallized from a mixture of methanol and ethyl acetate. yield: 0.80 g, 98% of pure (S)-(7). m.p. 119-121° C.; 1H NMR (200 Mhz, CD3OD) δ6.96 (s, 2H, NCHCHN); 3.96 (m, 1H, CHCH3); 2.4-2.65 (ABX, 3JH-H=6.3 Hz, 3JHb-H=6.7 Hz, 3JHa-Hb=14.5 Hz, CH2); 0.87 (d, 3H, 3JH-H=6.3 Hz, CH3); 13C NMR (50 MHz, CD3OD) δ145.8 (s, CH2CNH); 121.2 (d, NCH═CHNH); 67.1 (d, CHOH); 38.4 (t, CH2); 23.1 (q, CH3); MS (CI): [M+1]+. 127

1. concentrationThe mixture was concentrated in vacuo
2. additiona white precipitate appeared upon addition of 50 ml
3. distillationof cold distilled water
4. temperatureThe mixture was chilled
5. filtrationfiltered
6. washthe white precipitate was washed
7. distillationwith cold distilled water (10 ml)
8. customThe filtrate was then evaporated twice
9. dissolutionthe residual yellow oil redissolved in 50 ml dry methanol
10. customThe solution was then evaporated
11. customto yield a solid residue that
12. customcould be recrystallized from a mixture of methanol and ethyl acetate

ORD record

ord-801a2a56244846a898e4dc09dcad072b

Source dataset

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06476216B1