Hydrochloric Acid → HCID 178449570, compound

HRID 1752907Notes

Reaction equation

HRID 1752907 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-7b138389e42640f78b740c1b6dd1cb47
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

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