18-Crown-6 → (S)-2-(2-Fluoro-6-nitrobenzamido)propanoic acid

HRID 1399463Notes

Reaction equation

HRID 1399463 reaction equation
[F-:1].[K+].[N+:3]([C:6]1[CH:19]=[CH:18][CH:17]=[C:16]([N+]([O-])=O)[C:7]=1[C:8]([NH:10][C@@H:11]([CH3:15])[C:12]([OH:14])=[O:13])=[O:9])([O-:5])=[O:4].C1OCCOCCOCCOCCOCCOC1>CS(C)=O>[F:1][C:16]1[CH:17]=[CH:18][CH:19]=[C:6]([N+:3]([O-:5])=[O:4])[C:7]=1[C:8]([NH:10][C@@H:11]([CH3:15])[C:12]([OH:14])=[O:13])=[O:9]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 86713105(S)-2-(2,6-dinitrobenzamido)propanoic acid

Product 1

HCID 86713132(S)-2-(2-Fluoro-6-nitrobenzamido)propanoic acidYield 63%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of spray-dried KF (1.02 g, 17.6 mmol), intermediate 13 (500 mg, 1.76 mmol) and catalytic amount of 18-crown-6 in dry DMSO (10 mL) was stirred at 170-180° C. for 45 min. Work-up of the reaction mixture as described in example 1 gave the product as a pale brown color solid (284 mg, 63%), mp 142-144° C. 1H NMR (400 MHz, DMSO-d6): δ 9.05 (1H, d, J=7.2 Hz), 8.01 (1H, dd, J=6.6, 1.8 Hz), 7.72-7.78 (2H, m), 4.44 (1H, pentet, J=7.2 Hz), 1.34 (3H, d, J=7.2 Hz); LC-MS (positive ion mode): m/z 279 (M+Na)+.

Sources & evidence

ORD record
ord-d767f8d3d248441bba381ff03f11d831
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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