Hydrochloric Acid → HCID 178509684, compound

HRID 1622133Notes

Reaction equation

HRID 1622133 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:24]C)=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16]C(=O)OC(C)(C)C)[CH:10]=2)[CH:8]=1)#[N:2].[N:26]([Sn](CCCC)(CCCC)CCCC)=[N+:27]=[N-:28].C(OCC)(=O)C.Cl>C1(C)C=CC=CC=1>[NH2:16][CH2:15][C:11]1[CH:10]=[C:9]([C:7]2[C:6]([OH:24])=[CH:5][CH:4]=[C:3]([C:1]3[NH:2][N:28]=[N:27][N:26]=3)[CH:8]=2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4984872Tributyltin azideHCID 86607705Tert-butyl (5'-cyano-2'-methoxybiphenyl-3-ylmethyl)carbamate

Product 1

HCID 178509684HCID 178509684, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl (5′-cyano-2′-methoxy-biphenyl-3-yl-methyl)-carbamate (0.73 g, 2.16 mmol), prepared as in Reference 19, and azidotributyltin (0.9 mL, 3.2 mmol) was dissolved in toluene (5 mL) and the solution was refluxed for 14 hours. The mixture cooled to room temperature and then workup with ethyl acetate and 1N HCl gave a slurry. The slurry was dried by rotovap and then triturated with hexanes. The solids were collected by filtration and treated with hydrobromic acid (48% aqueous, 15 mL). The mixture was refluxed for 14 hours at 120° C. and then diluted with water (50 mL). The dilution was dried by lyophilization to give 3′-aminomethyl-5-(1H-tetrazol-5-yl)-biphenyl-2-ol (0.4 g).

Workup

  1. temperaturethe solution was refluxed for 14 hours
  2. customgave a slurry
  3. customThe slurry was dried by rotovap
  4. customtriturated with hexanes
  5. filtrationThe solids were collected by filtration
  6. additiontreated with hydrobromic acid (48% aqueous, 15 mL)
  7. temperatureThe mixture was refluxed for 14 hours at 120° C.
  8. additiondiluted with water (50 mL)
  9. customThe dilution was dried by lyophilization

Sources & evidence

ORD record
ord-d9f8a51b29174bd8a9b31fc4c1f88f78
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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