Sodium Carbonate → (R)-2-(2,6-Dinitrobenzamido)propanoic acid

HRID 1399439Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[NH2:16][C@@H:17]([C:19]([OH:21])=[O:20])[CH3:18].C([O-])([O-])=O.[Na+].[Na+].[N+](C1C=CC=C([N+]([O-])=O)C=1C(O)=O)([O-])=O>>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=1[C:6]([NH:16][C@H:17]([CH3:18])[C:19]([OH:21])=[O:20])=[O:7])([O-:3])=[O:2]

Participants

Reactant 4

HCID 10340Sodium Carbonate

HCID 71080D-Alanine

HCID 119206Benzoic acid, 2,6-dinitro-

HCID 222422992,6-Dinitrobenzoyl chloride

Product 1

HCID 86713115(R)-2-(2,6-Dinitrobenzamido)propanoic acid

Procedure

The reaction of 2,6-dinitrobenzoyl chloride (prepared from 2,6-dinitrobenzoic acid, 1.4 g and SOCl2, 15 mL) with D-alanine (0.7 g, 7.92 mmol) in the presence of Na2CO3 (0.83 g, 7.92 mmol) as described in intermediate 2 gave the title compound as a pale brown color solid (1.58 g, 85%), mp 202-204° C. 1H NMR (400 MHz, DMSO-d6): δ 12.79 (1H, br s), 9.24 (1H, d, J=7.6 Hz), 8.45 (2H, d, J=8.4 Hz), 7.93 (1H, t, J=8.4 Hz), 4.48 (1H, pentet, J=7.3 Hz), 1.33 (3H, d, J=7.2 Hz); LC-MS (negative ion mode): m/z 282 (M−H)−.

Sources & evidence

ORD record: ord-6fa30a287cf945d5a556643c19a86075
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906344B2

Reaction notes

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