Hydrochloric Acid → HCID 88540023, compound

Dichloromethane (20 mL) was added to the vial containing 3-methoxycyclobutanecarboxylic acid (1:1 isomers, 1500 mg, 11.53 mmol), N-methoxymethanamine.HCl (1514 mg, 15.53 mmol) and HATU (6570 mg, 17.3 mmol). Hunig's base (8.03 mL, 46.1 mmol) was then added. The mixture was stirred at room temperature overnight. The mixture was diluted with H2O and extracted with EtOAc three times. Insoluble solids were observed in the aqueous layer. The combined organic layers were washed with brined, dried over Na2SO4 and concentrated. The crude was dissolved in EtOAc and loaded to the column and purified by CombiFlash (40 g silica gel, EtOAc/heptane: 0→50%), leading to less polar diastereomer A and slightly more polar diastereomer B. Diastereomer A: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.09-2.25 (m, 2H) 2.43-2.57 (m, 2H) 3.17 (s, 3H) 3.23 (s, 3H) 3.43 (m, 1H) 3.63 (s, 3H) 3.98-4.09 (m, 1H). GCMS: observed 173 for C8H15NO3.

1. extractionextracted with EtOAc three times
2. washThe combined organic layers were washed with brined,
3. dry with materialdried over Na2SO4
4. concentrationconcentrated
5. dissolutionThe crude was dissolved in EtOAc
6. custompurified by CombiFlash (40 g silica gel, EtOAc/heptane: 0→50%)

ORD record

ord-dba35bc9a85040e9b170b95f2e7dab96

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056834B2