Ammonia → HCID 25417766, compound

Temperature

0 °C

TEA (10.4 mL, 74.5 mmol) was added to a 0° C. solution of Boc-L-azetidine-2-carboxylic acid (7.50 g, 37.3 mmol) in THF (85 mL) and the resulting mixture was stirred at 0° C. for 20 min, before ethyl chloroformate (3.82 mL, 39.1 mmol) was added (exotherm). The rxn mixture was stirred at 0° C. for 20 min, then 25% aq. NH3 (62.7 mL, 447 mmol) in THF (25 mL) was added and the resulting mixture was allowed to reach rt and stirring was continued at rt for 45 min. The mixture was concentrated in vacuo to remove the solvent, the residue was taken up in DCM and water, the org. layer was separated and the inorg. layer was extracted with DCM (2×). The combined org. layers were dried (MgSO4), filtered and concentrated in vacuo to yield the title compound C-1 as a white solid which was used further without purification. LC-MS A: tR=0.52 min; [M+H]+=201.27.

1. additionwas added (exotherm)
2. customto reach rt
3. stirringstirring
4. waitwas continued at rt for 45 min
5. concentrationThe mixture was concentrated in vacuo
6. customto remove the solvent
7. customlayer was separated
8. extractionlayer was extracted with DCM (2×)
9. dry with materiallayers were dried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-a7f086d01c1d4822b9c7c0a94ba44d6c

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403813B2