L-Alanine → (S)-2-(2,6-dinitrobenzamido)propanoic acid

HRID 1399438Notes

Reaction equation

HRID 1399438 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].C([O-])([O-])=O.[Na+].[Na+].[N+:13]([C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:17]=1[C:18](O)=[O:19])([O-:15])=[O:14]>[N+](C1C=CC=C([N+]([O-])=O)C=1C(Cl)=O)([O-])=O>[N+:13]([C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:17]=1[C:18]([NH:1][C@@H:2]([CH3:3])[C:4]([OH:6])=[O:5])=[O:19])([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 10340Sodium CarbonateHCID 119206Benzoic acid, 2,6-dinitro-

Product 1

HCID 86713105(S)-2-(2,6-dinitrobenzamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 222422992,6-Dinitrobenzoyl chlorideSolvent

Procedure

The reaction of 2,6-dinitrobenzoyl chloride (prepared from 2,6-dinitrobenzoic acid, 1 g and SOCl2, 10 mL) with L-alanine (0.52 g, 5.895 mmol) in the presence of Na2CO3 (0.625 g, 5.895 mmol) as described in intermediate 2 gave the title compound as a pale brown color solid (1.06 g, 80%), mp 222-224° C. 1H NMR (400 MHz, DMSO-d6): δ 12.81 (1H, br s), 9.23 (1H, d, J=7.6 Hz), 8.45 (2H, d, J=8.4 Hz), 7.92 (1H, t, J=8.2 Hz), 4.47 (1H, pentet, J=7.2 Hz), 1.33 (3H, d, J=7.2 Hz); LC-MS (negative ion mode): m/z 282 (M−H)−.

Sources & evidence

ORD record
ord-d7fbf88474444f59a0a02a79489c3c1e
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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