1-Methylimidazole → HCID 58712131, compound

To a solution of N-t-Boc-glycine (357 mg, 2 mmol) and N-methyl-imidazole (0.162 mL, 2 mmol) in THF (16 mL) cooled with ice methanesulfonyl chloride (0.158 mL, 2 mmol) was added. Ice batch was removed, compound 5 (0.4 g, 1 mmol) was added as a solid, followed by thriethylamine (0.144 mL, 2.02 mmol), and the reaction mixture was stirred at 40-50° C. overnight. A resulted solution was decanted from a solid, a flask rinsed with EtOAc, and a combined organic solution was washed with saturated ammonium chloride solution, then twice with water, brine and dried over anhydrous sodium sulfate. The solution was filtered out through a celite pad, concentrated and the residue was dissolved in 2-propanol (3 mL) with heating, and hexane (1-2 mL) was added drop-wise to start precipitation. In 1 hour a solid was filtered out, washed with 1:1 Hexane: ether mixture (10 ml×2) and vacuum-dried to give compound 6, 0.49 g (93.7%), LC purity 99 %. 1H NMR (DMSO-d6): δ 9.11 (s, 1H), 8.81 (s, 1H), 8.22 (s, 1H), 7.24 (m,1H), 7.20-7.15 (m, 2H), 6.91 (s, 2H), 3.87 (s, 3H), 3.73 (m, 2H), 3.70 (s, 3H), 3.66 (s, 6H). 1.40 (s, 9H).

1. additionwas added
2. customIce batch was removed
3. customA resulted solution was decanted from a solid, a flask
4. washrinsed with EtOAc
5. washa combined organic solution was washed with saturated ammonium chloride solution
6. dry with materialtwice with water, brine and dried over anhydrous sodium sulfate
7. filtrationThe solution was filtered out through a celite pad
8. concentrationconcentrated
9. dissolutionthe residue was dissolved in 2-propanol (3 mL)
10. temperaturewith heating
11. additionhexane (1-2 mL) was added drop-wise
12. customprecipitation
13. filtrationIn 1 hour a solid was filtered out
14. washwashed with 1:1 Hexane
15. dry with materialether mixture (10 ml×2) and vacuum-dried

ORD record

ord-cb7371730d024544968be61a37899056

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884094B2