Guanidine Hydrochloride → HCID 19874547, compound

HRID 465432Notes

Reaction equation

HRID 465432 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[CH:6]([OH:24])[CH2:7][NH:8][CH:9]([CH3:23])[CH2:10][C:11]1[CH:22]=[CH:21][C:14]([CH:15]([OH:20])[C:16](OC)=[O:17])=[CH:13][CH:12]=1.Cl.[NH2:31][C:32]([NH2:34])=N.[Na]>CO>[NH2:31][C:32]1[O:20][CH:15]([C:14]2[CH:21]=[CH:22][C:11]([CH2:10][CH:9]([NH:8][CH2:7][CH:6]([OH:24])[C:5]3[CH:25]=[CH:26][CH:27]=[C:3]([C:2]([F:1])([F:28])[F:29])[CH:4]=3)[CH3:23])=[CH:12][CH:13]=2)[C:16](=[O:17])[N:34]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 19874571HCID 19874571, compound

Product 1

HCID 19874547HCID 19874547, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of methyl 4-[2-[(3-trifloromethyl-β-hydroxyphenethyl)amino]propyl]mandelate (1.5 g) and guanidine hydrochloride (0.35 g) in methanol at room temperature was added a solution of sodium (0.084 g) in methanol. The solution was heated under reflux for 2 h., cooled, filtered and the solvent removed in vacuo. The residue was partitioned between ethyl acetate, and water, the organic layer separated, dried (magnesium sulphate), and evaporated to an oil which was chromatographed on silica. Elution with chloroform:methanol (95:5) gave 2-amino 5-[4-[2[(3-trifluoromethyl-β-hydroxyphenethyl)amino]propyl]phenyl]oxazol-4-one (0.45 g) as a 40:60 mixture of diastereoisomers, m.p. 152°-164° C. (acetone).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 2 h.
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe residue was partitioned between ethyl acetate, and water
  7. customthe organic layer separated
  8. dry with materialdried (magnesium sulphate)
  9. customevaporated to an oil which
  10. customwas chromatographed on silica
  11. washElution with chloroform:methanol (95:5)

Sources & evidence

ORD record
ord-3fab42825c8e48dfb5b6a4340aa112a3
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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