(S)-Methyl 2-amino-6-((tert-butoxycarbonyl)amino)hexanoate → N-[N-(3,5-Difluorophenylacetyl)-L-alaninyl]-Nepsilon-(tert-butoxycarbonyl)-L-lysine Methyl Ester

HRID 322722

Reaction equation

HRID 322722 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([OH:17])=O)[CH3:14])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[CH3:18][O:19][C:20](=[O:35])[C@H:21]([CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH2:22]>>[CH3:18][O:19][C:20](=[O:35])[C@H:21]([CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[NH:22][C:15](=[O:17])[C@H:13]([CH3:14])[NH:12][C:10](=[O:11])[CH2:9][C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=1

Participants

3

Reactant 2

HCID 7018776(S)-Methyl 2-amino-6-((tert-butoxycarbonyl)amino)hexanoateHCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid

Product 1

HCID 20642604N-[N-(3,5-Difluorophenylacetyl)-L-alaninyl]-Nepsilon-(tert-butoxycarbonyl)-L-lysine Methyl Ester

Procedure

Following General Procedure A and using N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and Nε-(tert-butoxycarbonyl)-L-lysine methyl ester (Bachem), the title compound was prepared as an oil. The reaction was monitored by tlc (Rf=0.40 in 50% EtOAc/hexanes) and the product was purified by flash chromotography using 50% EtOAc/hexanes as the eluent.

Workup

  1. customthe product was purified by flash chromotography

Sources & evidence

ORD record
ord-b8ac866f51894f699edcab131f6d81aa
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Linked notes

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