Hydrochloric Acid → HCID 66665931, compound

HRID 925454Notes

Reaction equation

HRID 925454 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C:8]([NH:13][C:14](=[O:17])[CH2:15]Cl)([CH2:11][OH:12])[CH2:9][OH:10])[CH:7]=1.CC(C)([O-])C.[K+].Cl.O>CC(O)(C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C:8]2([CH2:11][OH:12])[NH:13][C:14](=[O:17])[CH2:15][O:10][CH2:9]2)[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 66665606N-[1-(5-Bromo-2-fluoro-phenyl)-2-hydroxy-1-hydroxymethyl-ethyl]-2-chloro-acetamide

Product 1

HCID 66665931HCID 66665931, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of N-[1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-hydroxymethyl-ethyl]-2-chloro-acetamide (6.34 g, 18.62 mmol) and potassium tert.-butoxide (2.09 g, 18.62 mmol) in 62 ml tBuOH was refluxed for 30 min. 19 ml 1 N HCl and water were added and the aqueous layer was extracted with EtOAc. The organic layer was washed with brine, dried with MgSO4 and evaporated. The crude product was recrystallized in Hex/EtOAc to provide the title compound as an off-white solid.

Workup

  1. temperaturewas refluxed for 30 min
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. customevaporated
  6. customThe crude product was recrystallized in Hex/EtOAc

Sources & evidence

ORD record
ord-1a416a1d1f93493cbb034c79cf60753f
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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