Sodium sulfate decahydrate → HCID 25050520, compound

HRID 1020246Notes

Reaction equation

HRID 1020246 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]([CH:27]=[CH:28][CH:29]=1)[CH2:11][NH:12][C:13](=[O:26])[NH:14][C:15]1[S:16][CH:17]=[C:18]([CH2:20][C:21](OCC)=[O:22])[N:19]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)[O-].[Na+]>C1COCC1>[F:7][C:8]1[CH:9]=[C:10]([CH:27]=[CH:28][CH:29]=1)[CH2:11][NH:12][C:13]([NH:14][C:15]1[S:16][CH:17]=[C:18]([CH2:20][CH2:21][OH:22])[N:19]=1)=[O:26]

Participants

6

Reactant 4

HCID 62649Sodium sulfate decahydrateHCID 516919Sodium BisulfateHCID 21226445Aluminium lithium hydrideHCID 86622747HCID 86622747, compound

Product 1

HCID 25050520HCID 25050520, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (10.6 μL, 10.6 mmol, 1M in THF) was added dropwise to a THF (50 mL) solution of ethyl 2-(2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)acetate (1.32 g, 4.1 mmol) at −78° C. The reaction was allowed to slowly warm to ambient temperature. The mixture was stirred at ambient temperature until completion of the reaction. Sodium sulfate decahydrate (3.2 g, 10 mmol) was added carefully. It was followed by the addition of sodium bisulfate (1.8 g) and the mixture was stirred for 30 hours. An aqueous work-up with EtOAc and a recrystallization from a mixture of CH2Cl2 and hexane afforded the pure title compound. 1H NMR (400 MHz, CDCl3): 9.5 (s, 1H, br), 7.75 (s, 1H, br), 7.27 (m, 1H), 7.07 (d, 1H), 7.01 (d, 1H), 7.94 (td, 1H), 6.48 (s, 1H), 4.48 (d, 2H), 3.83 (t, 2H), 2.83 (t, 2H). MS (ES+): M/Z 338 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 30 hours
  2. customAn aqueous work-up with EtOAc and a recrystallization
  3. additionfrom a mixture of CH2Cl2 and hexane

Sources & evidence

ORD record
ord-47175f6eda8f4cd99e6c11910bf2ef79
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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