(-)-2-Aminobutyric acid → Methyl N-[N-(3-nitrophenylacetyl)-L-alaninyl]-(S)-2-aminobutanoate

HRID 1016947Notes

Reaction equation

HRID 1016947 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][CH3:27])[C:22]([O:24][CH3:25])=[O:23].N[C@@H](CC)C(O)=O>>[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][CH3:27])[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 3

HCID 80283(-)-2-Aminobutyric acidHCID 53788870N-(3-Nitrophenylacetyl)-L-alanineHCID 71313169(S)-methyl 2-aminobutanoate hydrochloride

Product 1

HCID 22894965Methyl N-[N-(3-nitrophenylacetyl)-L-alaninyl]-(S)-2-aminobutanoate

Procedure

Following General Procedure C and using N-(3-nitrophenylacetyl)-L-alanine (from Example D11 above) and methyl (S)-2-aminobutanoate hydrochloride prepared from (S)-(+)-2-aminobutyric acid (Aldrich) using General Procedure H), the title compound was prepared as a solid (mp=154-157° C.).

Sources & evidence

ORD record
ord-4c2f1790e37e4ed1a06e4fa1bfe200a0
Source dataset
uspto-grants-2002_11
Patent number
US06476263B1

Reaction notes

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