p-Toluenesulfonic acid → HCID 54543058, compound

HRID 2247905Notes

Reaction equation

HRID 2247905 reaction equation
[N:1]1([CH:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:18])[O:15][CH2:16][CH3:17])=[C:9]([CH2:19][O:20]C3CCCCO3)[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[OH:20][CH2:19][C:9]1[CH:8]=[C:7]([CH:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:12]=[CH:11][C:10]=1[NH:13][C:14](=[O:18])[O:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 54045049HCID 54045049, compound

Product 1

HCID 54543058HCID 54543058, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 10.5 parts of intermediate 60, namely ethyl [4-[(1H-imidazol-1-yl)phenylmethyl]-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl]carbamate, 5.5 parts of 4-methylbenzenesulfonic acid and 198 parts of ethanol was stirred over weekend at room temperature and for a short time at 50°-60° C. After cooling, there were added ethanol and Na2CO3. The whole was stirred for 15 min. and was then filtered. The filtrate was evaporated and the residue was partitioned between dichloromethane and water. The organic layer was separated and the aqueous layer was re-extracted with dichloromethane. The combined dichloromethane layers were dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CHCl3 /CH3OH 95:5). The eluent of the desired fraction was evaporated and the residue was co-evaporated with methylbenzene. The crystallized product was filtered off, stirred in 2,2'-oxybispropane and dried in vacuo, yielding 4.65 parts (46.0%) of ethyl [2-(hydroxymethyl)-4-[(1H-imidazol-1-yl)phenylmethyl]phenyl]carbamate; mp. 143.1° C. (interm. 61).

Workup

  1. temperatureAfter cooling
  2. filtrationwas then filtered
  3. customThe filtrate was evaporated
  4. customthe residue was partitioned between dichloromethane and water
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was re-extracted with dichloromethane
  7. dry with materialThe combined dichloromethane layers were dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography (silica gel; CHCl3 /CH3OH 95:5)
  11. customThe eluent of the desired fraction was evaporated
  12. filtrationThe crystallized product was filtered off
  13. stirringstirred in 2,2'-oxybispropane
  14. customdried in vacuo

Sources & evidence

ORD record
ord-9c69862fafff4ac2adddbde28167a9e3
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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