Triethylamine → HCID 131736931, compound

Temperature

30 °C

To a solution of Racemate-ethyl 3-(benzyloxycarbonylamino)-4-hydroxycyclohexanecarboxylate (7.0 g, 22 mmol) and triethylamine (6.7 g, 66 mmol) in dichloromethane (100 mL) was dropwise added methanesulfonyl chloride (5.1 g, 44 mmol) at 0° C., and the mixture was stirred at this temperature for 2 hours. The reaction mixture was washed with water (200 mL×3) and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to thereby give crude product (8.0 g, crude) as a yellow oil. A mixture of the above residue (8.0 g, 20 mmol) and sodium azide (7.8 g, 120 mmol) in dimethylsulfoxide (50 mL) was stirred at 100° C. for 18 hours. The reaction mixture was cooled to ˜30° C., dissolved in water (˜300 mL) and extracted with ethyl acetate (200 mL×2). The combined organic layers were washed with brine (˜200 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (3.5 g, 46% total yield for two steps) as a colorless oil. MS (ES+) C17H22N4O4 requires: 346, found: 347 [M+H]+, 369 [M+Na]+.

1. customat 0° C.
2. washThe reaction mixture was washed with water (200 mL×3) and brine
3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto thereby give crude product (8.0 g, crude) as a yellow oil
7. stirringwas stirred at 100° C. for 18 hours
8. extractionextracted with ethyl acetate (200 mL×2)
9. washThe combined organic layers were washed with brine (˜200 mL)
10. dry with materialdried over anhydrous sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-620232012f4a4d33a93774f0ac0c1cd5

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434700B2