[(N-benzyloxycarbonyl-L-alanyl)amino]-methylphosphonic acid → (L-alanylamino)-methylphosphonic acid

63.2 g of [(N-benzyloxycarbonyl-L-alanyl)amino]-methylphosphonic acid in a mixture of 600 ml of methanol and 20 ml of concentrated hydrochloric acid were hydrogenated at room temperature and atmospheric pressure in the presence of 6.0 g of 10% palladium-on-charcoal catalyst until absorption of hydrogen ceased. The catalyst was filtered off and washed with methanol. The filtrate was treated with 30 ml of propylene oxide and the mixture stored overnight in a refrigerator. The solid was filtered off, washed with methanol and ether and dried over phosphorus pentoxide in vacuo. The solid was taken up in 80 ml of boiling water, filtered and treated with 120 ml of ethanol. The mixture was cooled and then refrigerated overnight. The solid was filtered off, washed well with ethanol and dried over phosphorus pentoxide in vacuo. There were obtained 31.85 g of (L-alanylamino) -methylphosphonic acid of melting point 293°-294° C (decomposition); [α]D20 = 33.8° (c =1% in water).

1. customwere hydrogenated at room temperature
2. customatmospheric pressure in the presence of 6.0 g of 10% palladium-on-charcoal catalyst until absorption of hydrogen
3. filtrationThe catalyst was filtered off
4. washwashed with methanol
5. additionThe filtrate was treated with 30 ml of propylene oxide
6. filtrationThe solid was filtered off
7. washwashed with methanol and ether
8. dry with materialdried over phosphorus pentoxide in vacuo
9. filtrationfiltered
10. additiontreated with 120 ml of ethanol
11. temperatureThe mixture was cooled
12. customrefrigerated overnight
13. filtrationThe solid was filtered off
14. washwashed well with ethanol
15. dry with materialdried over phosphorus pentoxide in vacuo

ORD record

ord-30ac6b3642624c99a4622326335f68c5

Source dataset

uspto-grants-1977_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04016148