HCID 11019715, compound → HCID 18637944, compound

HRID 1164896Notes

Reaction equation

HRID 1164896 reaction equation
[N:1]1[N:2]=[N:3][N:4]2[CH:9]=[C:8]([C@@H:10]3[CH2:12][O:11]3)[CH:7]=[CH:6][C:5]=12.[NH2:13][C:14]([CH3:26])([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[CH3:15]>C(O)C>[CH3:26][C:14]([NH:13][CH2:12][C@@H:10]([C:8]1[CH:7]=[CH:6][C:5]2[N:4]([N:3]=[N:2][N:1]=2)[CH:9]=1)[OH:11])([CH3:15])[CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 11019715HCID 11019715, compoundHCID 13090314(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxirane

Product 1

HCID 18637944HCID 18637944, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 509 mg (3.13 mmol) of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane and 619 mg (3.21 mmol) of 2-amino-2-methyl-4-(4-methoxyphenyl)butane in 25 ml of absolute ethanol was heated at reflux for two hours and then stirred overnight at room temperature. The reaction mixture was concentrated and the residue chromatographed on silica gel (4:1:2 ethyl acetate:n-propanol:water with 1% NH4OH) to give 497 mg of product. Recrystallization from isopropanol afforded 357 mg of crystalline tetrazole, mp. 139-40° C.

Workup

  1. temperatureat reflux for two hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue chromatographed on silica gel (4:1:2 ethyl acetate:n-propanol:water with 1% NH4OH)

Sources & evidence

ORD record
ord-2f77c150f8da488bbebb2b15eae1a4e0
Source dataset
uspto-grants-1990_03
Patent number
US04906645

Reaction notes

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