Ethyl L-valinate hydrochloride → N-[N-[N-(3-Nitrophenylacetyl)-L-alaninyl]-threoninyl]-L-valine Ethyl Ester

HRID 322754Notes

Reaction equation

HRID 322754 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C@H:14]([C:16]([NH:18][C@H:19]([C:23]([OH:25])=O)[C@@H:20]([CH3:22])[OH:21])=[O:17])[CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH2:27]([O:29][C:30](=[O:36])[C@H:31]([CH:33]([CH3:35])[CH3:34])[NH2:32])[CH3:28]>C(Cl)(Cl)Cl.CO>[CH2:27]([O:29][C:30](=[O:36])[C@H:31]([CH:33]([CH3:35])[CH3:34])[NH:32][C:23](=[O:25])[C@H:19]([C@@H:20]([CH3:22])[OH:21])[NH:18][C:16](=[O:17])[C@H:14]([CH3:15])[NH:13][C:11](=[O:12])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH3:28]

Participants

4

Reactant 2

HCID 87181Ethyl L-valinate hydrochlorideHCID 22895020N-[N-(3-nitrophenylacetyl)-L-alaninyl]-L-threonine

Product 1

HCID 22895042N-[N-[N-(3-Nitrophenylacetyl)-L-alaninyl]-threoninyl]-L-valine Ethyl Ester

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following General Procedure C and using N-[N-(3-nitrophenylacetyl)-L-alaninyl]-L-threonine (prepared from N-[N-(3-nitrophenylacetyl)-L-alaninyl]-L-threonine methyl ester (from Example 144 above) using General Procedure AF) and L-valine ethyl ester hydrochloride (Aldrich), the title compound was prepared as a solid. The reaction was monitored by tlc (Rf=0.1 in 96:4 CHCl3/MeOH) and the product was purified by silica gel chromatography using 96:4 CHCl3/MeOH as the eluent.

Workup

  1. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0ca37cdbc3944dd99328036a3cb901f1
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

Loading…