18-Crown-6 → HCID 61708911, compound

HRID 1399459Notes

Reaction equation

HRID 1399459 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 86713104(S)-2-(2,4-dinitrobenzamido)propanoic acid

Product 1

HCID 61708911HCID 61708911, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of spray-dried KF (410 mg, 7.06 mmol), intermediate 11 (200 mg, 0.706 mmol) and catalytic amount of 18-crown-6 in dry DMSO (5 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 (117 mg, 65%), mp 136-138° C. 1H NMR (400 MHz, DMSO-d6): 812.74 (1H, br s), 8.96 (1H, d, J=7.2 Hz), 8.21 (1H, d, J=9.6 Hz), 8.16 (1H, d, J=8.4 Hz), 7.82 (1H, t, J=7.6 Hz), 4.42 (1H, pentet, J=7.0 Hz), 1.38 (3H, d, J=7.2 Hz); LC-MS (negative ion mode): m/z 255 (M−H)−.

Sources & evidence

ORD record
ord-eaf4fbbb1c924dea96ae1bac58726fee
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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