(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxirane → HCID 18637941, compound

HRID 1164898Notes

Reaction equation

HRID 1164898 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]([CH3:25])([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=1)[CH3:15]>C(O)C>[CH3:25][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:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=1

Participants

4

Reactant 2

HCID 13090314(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxiraneHCID 19863682HCID 19863682, compound

Product 1

HCID 18637941HCID 18637941, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 194 mg (1.21 mmol) of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane and 195 mg of 2-amino-2-methyl-4-(3-hydroxyphenyl)butane in 25 ml of absolute ethanol was heated at reflux for 6.5 hours. The reaction mixture was concentrated and the residue chromatographed on silica gel (4:1:2:1 ethyl acetate:n-propanol:water:ammonium hydroxide) to give 137 mg of product.

Workup

  1. temperatureat reflux for 6.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue chromatographed on silica gel (4:1:2:1 ethyl acetate:n-propanol:water:ammonium hydroxide)

Sources & evidence

ORD record
ord-0739fb0eae874bc5aae26850fa93b18f
Source dataset
uspto-grants-1990_03
Patent number
US04906645

Reaction notes

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