18-Crown-6 → (R)-2-(2-Fluoro-4-nitrobenzamido)propanoic acid

HRID 1399461Notes

Reaction equation

HRID 1399461 reaction equation
[F-:1].[K+].[N+]([C:6]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:7]=1[C:8]([NH:10][C@H:11]([CH3:15])[C:12]([OH:14])=[O:13])=[O:9])([O-])=O.C1OCCOCCOCCOCCOCCOC1>CS(C)=O>[F:1][C:6]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][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 86713114(R)-2-(2,4-Dinitrobenzamido)propanoic acid

Product 1

HCID 78976542(R)-2-(2-Fluoro-4-nitrobenzamido)propanoic acidYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of spray-dried KF (307 mg, 5.3 mmol), intermediate 12 (150 mg, 0.53 mmol) and catalytic amount of 18-crown-6 in dry DMSO (4 mL) was stirred at 170-180° C. for 30 min. Work-up of the reaction mixture as described in example 1 gave the product as a pale brown color solid (92 mg, 68%), mp 146-150° C. 1H NMR (400 MHz, DMSO-d6): δ 8.90 (1H, d, J=4.0 Hz), 8.21 (1H, d, J=9.6 Hz), 8.15 (1H, d, J=8.0 Hz), 7.84 (1H, t, J=6.8 Hz), 4.36-4.40 (1H, m), 1.38 (3H, d, J=6.4 Hz); LC-MS (negative ion mode): m/z 255 (M−H)−.

Sources & evidence

ORD record
ord-6da7bf46de8a4b60b0124043e72475f2
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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