Ethyl Acetate → HCID 10219671, compound

A solution of Example 1B (9.00 g, 38.5 mmol) and sodium bisulfite (3.80 g, 36.6 mmol) in water (200 mL) was stirred at 5° C. for 72 hours, warmed to ambient temperature, treated with a mixture of potassium cyanide (2.51 g, 38.6 mmol) in ethyl acetate (250 mL), and stirred for 4 hours. The separated ethyl acetate layer was washed sequentially with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was dissolved in dioxane (75 mL) and 12M HCl (75 mL), heated to reflux for 16 hours, concentrated, dissolved in water (8 mL) and acetone (300 mL), adjusted to pH 5.5 with 1M NaOH, and filtered. The filter cake was dried under vacuum to provide the desired product (5.81 g). MS (ESI(+)Q1MS) m/e 180 (M+H)+, 202 (M+Na)+; MS (ESI(−)) m/e 178 (M−H)−; 1H NMR (300 MHz, D2O) δ 4.25 (d, 0.5H), 4.14 (d, 0.5H), 3.78 (m, 0.5H), 3.66 (m, 0.5H), 2.65 (m, 2H), 2.13 (s, 1.5H), 2.09 (s, 1.5H), 1.93 (m, 2H).

1. washThe separated ethyl acetate layer was washed sequentially with water and brine
2. dry with materialdried (MgSO4)
3. filtrationfiltered
4. concentrationconcentrated
5. dissolutionThe concentrate was dissolved in dioxane (75 mL)
6. temperature12M HCl (75 mL), heated
7. temperatureto reflux for 16 hours
8. concentrationconcentrated
9. dissolutiondissolved in water (8 mL)
10. filtrationfiltered
11. customThe filter cake was dried under vacuum

ORD record

ord-a2108aafb02c487ca2caa1209cc9b05f

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07030262B2