Triethylamine → 1-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid

To azetidine-3-carboxylic acid (49.5 mmol, 5 g) in dioxane (150 ml), water (150 ml) and triethylamine (54.4 mmol, 7.58 ml) was added N-(benzyloxycarbonyloxy)succinimide (51.9 mmol, 12.94 g) and stirred at room temperature for half an hour. The reaction mixture was quenched with water and 30 ml of 2N hydrochloric acid and extracted three times with dichloromethane. The organic layers were combined, filtered through a phase separation filter and concentrated in vacuo. The residue was dissolved in dichloromethane and extracted three times with aqueous saturated sodium hydrogencarbonate solution. The aqueous layers were combined, acidified with 2N hydrochloric acid and extracted three times with dichloromethane. The organic layers were combined, washed with brine, filtered through a phase separation filter and concentrated in vacuo to give 1-(benzyloxycarbonyl)azetidine-3-carboxylic acid (10.27 g).

1. customThe reaction mixture was quenched with water and 30 ml of 2N hydrochloric acid
2. extractionextracted three times with dichloromethane
3. filtrationfiltered through a phase separation
4. filtrationfilter
5. concentrationconcentrated in vacuo
6. dissolutionThe residue was dissolved in dichloromethane
7. extractionextracted three times with aqueous saturated sodium hydrogencarbonate solution
8. extractionextracted three times with dichloromethane
9. washwashed with brine
10. filtrationfiltered through a phase separation
11. filtrationfilter
12. concentrationconcentrated in vacuo

ORD record

ord-53da7230223e42cdb15b9b467e6d8965

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658794B2