methyl (2S)-2-aminopentanoate hydrochloride → Methyl N-[N-(3-nitrophenylacetyl)-L-alaninyl]-(S)-2-aminopentanoate

HRID 322755Notes

Reaction equation

HRID 322755 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.[NH2:20][C@@H:21]([CH2:26][CH2:27][CH3:28])[C:22]([O:24][CH3:25])=[O:23]>C(Cl)(Cl)Cl.CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C@H:14]([C:16]([NH:20][C@@H:21]([CH2:26][CH2:27][CH3:28])[C:22]([O:24][CH3:25])=[O:23])=[O:18])[CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14118488methyl (2S)-2-aminopentanoate hydrochlorideHCID 53788870N-(3-Nitrophenylacetyl)-L-alanine

Product 1

HCID 22894966Methyl N-[N-(3-nitrophenylacetyl)-L-alaninyl]-(S)-2-aminopentanoate

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following General Procedure C and using N-(3-nitrophenylacetyl)-L-alanine (from Example D11 above) and methyl (S)-2-aminopentanoate hydrochloride (prepared from (S)-2-aminopentanoic acid (Novabiochem) using General Procedure H), the title compound was prepared as a solid. The reaction was monitored by tlc (Rf=0.4 in 9:1 CHCl3/MeOH).

Sources & evidence

ORD record
ord-8ba4e26444dd4ede8236510a13b4a31b
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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