Hydrochloric Acid → HCID 57948941, compound

HRID 1992289Notes

Reaction equation

HRID 1992289 reaction equation
[NH2:1][C@@:2]([C:8]1[CH:13]=[C:12]([Br:14])[C:11]([F:15])=[CH:10][C:9]=1[F:16])([CH3:7])[CH2:3][CH:4](O)[CH3:5].C([N:25]=[C:26]=[S:27])(=O)C1C=CC=CC=1.Cl>C1COCC1>[Br:14][C:12]1[C:11]([F:15])=[CH:10][C:9]([F:16])=[C:8]([C@:2]2([CH3:7])[CH2:3][CH:4]([CH3:5])[S:27][C:26]([NH2:25])=[N:1]2)[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68284Benzoyl isothiocyanateHCID 67025386HCID 67025386, compound

Product 1

HCID 57948941HCID 57948941, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a 0° C. solution of (4S)-4-amino-4-(5-bromo-2,4-difluorophenyl)pentan-2-ol (1.3 g, 4.4 mmoles) as a mixture of diastereomers in THF (50 mL) is added benzoyl isothiocyanate (1.4 g, 1.2 mmoles) dropwise and the reaction is stirred for 1 h. The reaction mixture is concentrated under reduced pressure. The residue is dissolved in dioxane (5 mL) and transferred to a thick-walled glass reaction vessel. To the mixture is added 5 N hydrogen chloride (75 mL, 375 mmoles) and the reaction is heated to 100° C. After 36 h, the solvent is removed under reduced pressure and the residue is dissolved in water. The water mixture is extracted with ethyl acetate. The aqueous phase is made basic with 5N NaOH and extracted with 3:1 chloroform:IPA. The chloroform: IPA phase is dried over sodium sulfate, filtered and the solvent removed under reduced pressure to give the title compound.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutionThe residue is dissolved in dioxane (5 mL)
  3. customtransferred to a thick-walled glass reaction vessel
  4. waitAfter 36 h
  5. customthe solvent is removed under reduced pressure
  6. dissolutionthe residue is dissolved in water
  7. extractionThe water mixture is extracted with ethyl acetate
  8. extractionextracted with 3:1 chloroform
  9. dry with materialThe chloroform: IPA phase is dried over sodium sulfate
  10. filtrationfiltered
  11. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-92a9186a215941b49c6a20a531956cd5
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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