Methyl L-threoninate hydrochloride → N-[N-(3-Nitrophenylacetyl)-L-alaninyl]-L-threonine Methyl Ester

HRID 1533653Notes

Reaction equation

HRID 1533653 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C@H:14]([C:16]([OH:18])=O)[CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH3:20][O:21][C:22](=[O:28])[C@H:23]([C@@H:25]([CH3:27])[OH:26])[NH2:24]>C(Cl)(Cl)Cl.CO>[CH3:20][O:21][C:22](=[O:28])[C@H:23]([C@@H:25]([CH3:27])[OH:26])[NH:24][C:16](=[O:18])[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

Participants

4

Reactant 2

HCID 2734893Methyl L-threoninate hydrochlorideHCID 53788870N-(3-Nitrophenylacetyl)-L-alanine

Product 1

HCID 22895021N-[N-(3-Nitrophenylacetyl)-L-alaninyl]-L-threonine Methyl Ester

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following General Procedure C and using N-(3-nitrophenylacetyl)-L-alanine (from Example D11 above) and L-threonine methyl ester hydrochloride (Aldrich), the title compound was prepared as a solid. The reaction was monitored by tlc (Rf=0.1 in 95:5 CHCl3/MeOH) and the product was purified by silica gel chromatography using 95:5 CHCl3/MeOH as the eluent.

Workup

  1. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2f2b1d04d84c4eb5b431fa0f89da9cd9
Source dataset
uspto-grants-2001_03
Patent number
US06207710B1

Reaction notes

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