Nalpha-Benzyl-Ndelta-Boc-Nalpha-Methylornithinyl 2-Naphthyl Ether → Ndelta-Boc-Nalpha-Methylornithinyl 2-Naphthyl Ether

HRID 1067102Notes

Reaction equation

HRID 1067102 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12](=[O:34])[C@H:13]([CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[N:14](CC1C=CC=CC=1)[CH3:15].[H][H]>[Pd]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12](=[O:34])[C@H:13]([CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[NH:14][CH3:15]

Participants

4

Reactant 2

HCID 131722658Nalpha-Benzyl-Ndelta-Boc-Nalpha-Methylornithinyl 2-Naphthyl EtherHCID 178418361HCID 178418361, compound

Product 1

HCID 131722660Ndelta-Boc-Nalpha-Methylornithinyl 2-Naphthyl Ether

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A methanolic solution of Nα-benzyl-Nδ-Boc-Nα-methylornithinyl 2-naphthyl ether (D) was reduced with hydrogen, over 5% palladium-on-carbon, to afford titled product: 1H NMR (400 MHz, CDCl3) δ1.44 (s, 9H), 1.63 (m, 2H), 1.95 (m, 2H), 2.53 (s, 3H), 2.95 (m, 1H), 3.09 (m, 2H), 4.01 (dd, J=10.7; 6.7 Hz, 1H), 4.12 (dd, J=10.5; 4.4 Hz, 1H), 7.19 (m, 2H), 7.35 (t, J=9.1 Hz, 1H), 7.45 (t, J=8.9 Hz, 1H), and 7.75 (m, 3H).

Sources & evidence

ORD record
ord-ae65839db3ae41ed8b8e01d7651b630b
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

Loading…