Hydrochloric Acid → HCID 178441746, compound

HRID 52895Notes

Reaction equation

HRID 52895 reaction equation
Cl.[CH2:2]([C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[N:39](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:38]=[N:37][N:36]=3)=[CH:25][CH:24]=2)[C:8]([C:17]([O:19]CC)=[O:18])=[C:9]([C:11]([CH2:15][CH3:16])([OH:14])[CH2:12][CH3:13])[N:10]=1)[CH2:3][CH2:4][CH3:5]>CO.C(OC(C)C)(C)C>[CH2:2]([C:6]1[N:7]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[NH:39][N:38]=[N:37][N:36]=3)=[CH:27][CH:28]=2)[C:8]([C:17]([OH:19])=[O:18])=[C:9]([C:11]([CH2:12][CH3:13])([OH:14])[CH2:15][CH3:16])[N:10]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19036251Ethyl 2-butyl-4-(1-ethyl-1-hydroxypropyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

Product 1

HCID 178441746HCID 178441746, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7914Diisopropyl EtherSolvent

Procedure

1.71 ml of 1N aqueous hydrochloric acid were added to a solution of 0.65 g of ethyl 2-butyl-4-(1-ethyl-1-hydroxypropyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in step (a) above] in 10 ml of methanol, and the resulting mixture was allowed to stand overnight at room temperature. At the end of this time, the solvent was removed by distillation under reduced pressure, and the concentrate was again dissolved in 10 ml of methanol. The resulting solution was mixed with 4.28 ml of a 1N aqueous solution of sodium hydroxide and then allowed to stand overnight at room temperature. The reaction mixture was then concentrated by evaporation under reduced pressure to remove the methanol. The pH of the concentrate was adjusted to a value of 3 by the addition of dilute aqueous hydrochloric acid, and the crystals which precipitated were collected by filtration. The crystals thus obtained were suspended in diisopropyl ether and then again collected by filtration and dried to give 0.35 g of the title compound, melting at 181°-183° C.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. dissolutionthe concentrate was again dissolved in 10 ml of methanol
  3. additionThe resulting solution was mixed with 4.28 ml of a 1N aqueous solution of sodium hydroxide
  4. waitto stand overnight at room temperature
  5. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  6. customto remove the methanol
  7. additionThe pH of the concentrate was adjusted to a value of 3 by the addition of dilute aqueous hydrochloric acid
  8. customthe crystals which precipitated
  9. filtrationwere collected by filtration
  10. customThe crystals thus obtained
  11. filtrationagain collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-5357a78f18a649a7829016e438e69171
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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