5-Aminovaleric acid → HCID 19808302, compound

5-Amino pentanoic acid (0.585 g, 5 m mol) was stirred for two days in dimethylformamide (5 ml) containing tetramethylguanidine (1.14 g, 10 m mol) and tert.butoxycarbonylazide (1.1 g, 7.5 m mol). The solution was evaporated and the residue partitioned between ethyl acetate (20 ml) and 10% citric acid solution (20 ml). The organic layer was washed with 10% citric acid (2×15 ml), water (3×15 ml) and brine 1×15 ml). Each aqueous wash was back extracted with ethyl acetate (20 ml). The combined organic layers were dried over anhydrous magnesium sulphate and evaporated to give an oil which slowly crystallised. Recrystallisation from diisopropyl ether/petrol gave 0.745 g (70% yield), mp. 47.5°-48.5° C., Rf silica gel 0.40 (benzene:dioxan:acetic acid 95:75:4).

1. customThe solution was evaporated
2. customthe residue partitioned between ethyl acetate (20 ml) and 10% citric acid solution (20 ml)
3. washThe organic layer was washed with 10% citric acid (2×15 ml), water (3×15 ml) and brine 1×15 ml)
4. washEach aqueous wash
5. extractionwas back extracted with ethyl acetate (20 ml)
6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulphate
7. customevaporated
8. customto give an oil which
9. customslowly crystallised
10. customRecrystallisation from diisopropyl ether/petrol
11. customgave 0.745 g (70% yield), mp. 47.5°-48.5° C., Rf silica gel 0.40 (benzene:dioxan:acetic acid 95:75:4)

ORD record

ord-1671bb606d144a2eabf97a87d3c6364a

Source dataset

uspto-grants-1980_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04198398