Sodium Sulfate → HCID 67266716, compound

HRID 601730Notes

Reaction equation

HRID 601730 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14][CH2:15][C@@H:16]([C:18](OC)=[O:19])[NH2:17].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[NH2:17][C@@H:16]([CH2:15][S:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[F:7])[CH2:18][OH:19]

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 67266706HCID 67266706, compound

Product 1

HCID 67266716HCID 67266716, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a round-bottom flask maintained under an inert atmosphere, 23.9 mL (23.9 mmoles) of lithium aluminum hydride (1M in THF) is introduced. The solution is cooled to 0° C. then 4.57 g (19.9 mmoles) of methyl S-(2-fluorophenyl)-L-cysteinate (3a-1) diluted in 21 mL of anhydrous THF is added. The solution is stirred at 0° C. for 1 hour then at ambient temperature for 30 minutes. The reaction medium is hydrolyzed by successive additions of 2.7 mL of water, 0.9 mL of 15% soda in water, then 0.9 mL of water. The suspension is stirred for 30 minutes at ambient temperature in the presence of sodium sulfate then filtered on a silica filter. The precipitate is washed with THF then the filtrate is concentrated under reduced pressure. A brown oil (3.56 g) is obtained that can be used without any additional purification in the following step.

Workup

  1. additionis introduced
  2. additionis added
  3. waitat ambient temperature for 30 minutes
  4. filtrationthen filtered on a silica
  5. filtrationfilter
  6. washThe precipitate is washed with THF
  7. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-ebde2c8f18454db5bc57dfe3ec4ec201
Source dataset
uspto-grants-2011_03
Patent number
US07902381B2

Reaction notes

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