Ethyl Acetate → HCID 11575909, compound

HRID 1713059Notes

Reaction equation

HRID 1713059 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:17])[CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[CH2:13][NH:12][C:11]1=[S:16])[CH3:4].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:29][C:28]([CH:30]=O)=[C:27]([C:32](OCC)=[O:33])[CH:26]=2)=[CH:21][CH:20]=1.C(OCC)(=O)C>C1COCC1.CCCCCC>[CH2:3]([O:5][C:6](=[O:17])[CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[C:13]2[N:12]([C:32](=[O:33])[C:27]3[CH:26]=[C:25]([C:22]4[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=4)[O:29][C:28]=3[CH:30]=2)[C:11]1=[S:16])[CH3:4]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2798516ethyl 5-(4-chlorophenyl)-2-formyl-3-furoateHCID 86618342HCID 86618342, compound

Product 1

HCID 11575909HCID 11575909, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

As further depicted in Scheme 40 below, NaH (88 mg of 60% oil dispersion, 53 mg, 2.2 mmol) is added in four portions over 10 minutes under a nitrogen atmosphere to a solution of 4-(5-oxo-2-thioxo-imidazolidin-1-yl)-butyric acid ethyl ester (230 mg, 1 mmol) and ethyl 5-(4-chlorophenyl)-2-formyl-3-furoate (293 mg, 1.05 mmol obtained from Maybridge Ltd.; Cat. No. SP 00067) in anhydrous THF (20 ml). After the ensuing mildly exothermic reaction is completed, the reaction mixture is refluxed for 8-10 hours while monitoring the reaction progress by TLC analysis using an ethyl acetate:hexane mixture as eluent. Thereafter the solvent is removed under reduced pressure, and 6 M HCl (50 ml) is added to the residue while cooling the reaction vessel. Ether (50 ml) is added and the resulting heterogeneous mixture is stirred vigorously at 0° C. for 20 minutes, filtered, washed with ether and water and the solvents are removed under heat at 50° C. overnight to give Compound 48.

Workup

  1. customAfter the ensuing mildly exothermic reaction
  2. temperaturethe reaction mixture is refluxed for 8-10 hours
  3. customThereafter the solvent is removed under reduced pressure, and 6 M HCl (50 ml)
  4. additionis added to the residue
  5. temperaturewhile cooling the reaction vessel
  6. additionEther (50 ml) is added
  7. filtrationfiltered
  8. washwashed with ether and water
  9. customthe solvents are removed
  10. temperatureunder heat at 50° C. overnight

Sources & evidence

ORD record
ord-d9a1e1b3254b452fb05425a76fde7bd0
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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