Hydrochloric Acid → HCID 178449570, compound

HRID 1622135Notes

Reaction equation

HRID 1622135 reaction equation
[C:1]([NH:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:21]=[C:20]([C:22]3[NH:26][N:25]=[N:24][N:23]=3)[CH:19]=[CH:18][C:17]=2[OH:27])[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)Cl.[OH-].[Na+].Cl.[C:35](OCC)(=[O:37])C>>[C:1]([NH:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:21]=[C:20]([C:22]3[NH:26][N:25]=[N:24][N:23]=3)[CH:19]=[C:18]([CH:35]=[O:37])[C:17]=2[OH:27])[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 178449569HCID 178449569, compound

Product 1

HCID 178449570HCID 178449570, compound

Procedure

1-tert-Butyl-3-[2′-hydroxy-5′-(1H-tetrazol-5-yl)-biphenyl-3-ylmethyl]-urea (0.56 g, 1.5 mmol) was dissolved in a mixture of chloroform (0.2 mL, 3 mmol) and sodium hydroxide (10% aqueous, 5 mL, 12 mmol) and the mixture was refluxed for 5 days. The mixture was worked up with 1N hydrochloric acid and ethyl acetate. Some solids precipitated out of solution and were filtered and dried. The organic layer from the extraction was dried and combined with the solids above gives 1-tert-butyl-3-[3′-formyl-2′-hydroxy-5′-(1H-tetrazol-5-yl)-biphenyl-3-ylmethyl]-urea as a 3:1 mixture of starting material to product.

Workup

  1. temperaturethe mixture was refluxed for 5 days
  2. customSome solids precipitated out of solution
  3. filtrationwere filtered
  4. customdried
  5. extractionThe organic layer from the extraction
  6. customwas dried

Sources & evidence

ORD record
ord-4889a19f0cf54ef2b6951dd82ecc92bd
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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