Dicyclohexylcarbodiimide → HCID 10176363, compound

DCC (3.02 g) was added to a solution of L-phenylalanine-N-benzylcarbamate (4.00 g) and N-hydroxysuccinimide (1.69 g) in dry THF (35 ml) at 0° C. The mixture was stirred at that temperature for 16 h and filtered through Celite. To the filtrate was added aqueous methylamine (40% aq., 5 ml) and the mixture was stirred at RT for 24 h. The reaction mixture was concentrated in vacuo and the crude material (6.01 g) was dissolved in ethanol (250 ml). A suspension of 10% palladium on carbon in H2O (ca 2 ml) was added to the ethanol solution in a bomb. The mixture was stirred in the presence of hydrogen at 724 kPa (105 psi) for 18 h. The solution was filtered through Celite and the filtrate was evaporated in vacuo. The residue was partioned between 1N hydrochloric acid (110 ml) and dichloromethane (50 ml). The layers were separated and the aqueous layer was extracted with dichloromethane (50 ml). The aqueous layer was basified with 3N sodium hydroxide solution to pH ~14 and extracted with dichloromethane (3×50 ml). The latter extracts were combined, dried (Na2SO4), filtered and evaporated, to give the title compound as a colourless viscous oil which solidified under high vacuum (2.24 g).

1. filtrationfiltered through Celite
2. additionTo the filtrate was added aqueous methylamine (40% aq., 5 ml)
3. stirringthe mixture was stirred at RT for 24 h
4. concentrationThe reaction mixture was concentrated in vacuo
5. dissolutionthe crude material (6.01 g) was dissolved in ethanol (250 ml)
6. additionA suspension of 10% palladium on carbon in H2O (ca 2 ml)
7. additionwas added to the ethanol solution in a bomb
8. stirringThe mixture was stirred in the presence of hydrogen at 724 kPa (105 psi) for 18 h
9. filtrationThe solution was filtered through Celite
10. customthe filtrate was evaporated in vacuo
11. customThe layers were separated
12. extractionthe aqueous layer was extracted with dichloromethane (50 ml)
13. extractionextracted with dichloromethane (3×50 ml)
14. dry with materialdried (Na2SO4)
15. filtrationfiltered
16. customevaporated

ORD record

ord-b953fb0020a24164bcbf2211deb06d35

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05853623