N-(Phenylacetyl)-L-alanine → N-[N-(Phenylacetyl)-L-alaninyl]-Nepsilon-(tert-butoxycarbonyl)-L-lysine Methyl Ester

HRID 983341Notes

Reaction equation

HRID 983341 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]([C:13]([OH:15])=O)[CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:17][O:18][C:19](=[O:34])[C@H:20]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[NH2:21].C(Cl)Cl.CO.[NH4+].[OH-]>>[CH3:17][O:18][C:19](=[O:34])[C@H:20]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[NH:21][C:13](=[O:15])[C@H:11]([CH3:12])[NH:10][C:8](=[O:9])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 7004640N-(Phenylacetyl)-L-alanineHCID 16218818L-Lysine, N6-[(1,1-dimethylethoxy)carbonyl]-, methyl ester, hydrochloride (1:1)HCID 21896990Dichloromethane methanol ammonium hydroxide

Product 1

HCID 69734775N-[N-(Phenylacetyl)-L-alaninyl]-Nepsilon-(tert-butoxycarbonyl)-L-lysine Methyl Ester

Procedure

Following General Procedure A and using N-(phenylacetyl)-L-alanine (from Example B1 above) and Nε-(tert-butoxycarbonyl)-L-lysine methyl ester hydrochloride (Bachem), the title compound was prepared as a solid (mp=119-121° C.). The reaction was monitored by tlc (Rf=0.46 in 90:10:1 CH2Cl2\MeOH\NH4OH).

Sources & evidence

ORD record
ord-3687178ec0b84dae94b376256a0270c7
Source dataset
uspto-grants-2005_03
Patent number
US06861558B2

Reaction notes

Loading…