Hydrochloric Acid → HCID 66812663, compound

HRID 13219Notes

Reaction equation

HRID 13219 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:3]=1[O:4][CH2:5][C@@H:6]([OH:20])[C@@H:7]([NH:9]C(=O)OCC1C=CC=CC=1)[CH3:8].[ClH:26]>C(O)C.C(OCC)C.[Pd]>[Cl-:26].[F:1][C:2]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:3]=1[O:4][CH2:5][C@@H:6]([OH:20])[C@@H:7]([NH3+:9])[CH3:8]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 59339687HCID 59339687, compound

Product 1

HCID 66812663HCID 66812663, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

Benzyl (2S,3S)-4-(2,4-difluorophenoxy)-3-hydroxybutan-2-ylcarbamate (426 mg, 1.21 mmol) in ethanol (20 mL) was hydrogenated over Pd (10% on carbon) (40.0 mg) at r.t. and atmospheric pressure overnight. The mixture was filtered through celite, evaporated, dissolved in ethanol and filtered through a syringe filter. On evaporation a white solid was obtained. This was dissolved in ethanol (4 mL) and diethyl ether (6 mL) and 1M HCl in diethyl ether was added (1.5 mL) under stirring. Evaporation, coevaporation from dichloromethane/diethylether gave the title compound as a solid, (290 mg, 94%).

Workup

  1. customatmospheric pressure overnight
  2. filtrationThe mixture was filtered through celite
  3. customevaporated
  4. dissolutiondissolved in ethanol
  5. filtrationfiltered through a syringe
  6. filtrationfilter
  7. customOn evaporation a white solid
  8. customwas obtained
  9. customEvaporation, coevaporation from dichloromethane/diethylether

Sources & evidence

ORD record
ord-0e8773a01b534a808bfcd44c8fa054b5
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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