tert-Butanol → tert-butyl 2-(3-phenyl-1H-1,2,4-triazol-1-yl)ethylcarbamate

HRID 1621104Notes

Reaction equation

[C:1]1([C:7]2[N:11]=[CH:10][N:9]([CH2:12][CH2:13]C(O)=O)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(N=[N+]=[N-])(=O)([O:25][C:26]1C=CC=CC=1)OC1C=CC=CC=1.C([N:38](CC)CC)C.[C:43]([OH:47])([CH3:46])([CH3:45])[CH3:44]>>[C:1]1([C:7]2[N:11]=[CH:10][N:9]([CH2:12][CH2:13][NH:38][C:26](=[O:25])[O:47][C:43]([CH3:46])([CH3:45])[CH3:44])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 123414Diphenylphosphoryl azide

HCID 124615483-(3-Phenyl-1H-1,2,4-triazol-1-yl)propionoic acid

Product 1

HCID 71279430tert-butyl 2-(3-phenyl-1H-1,2,4-triazol-1-yl)ethylcarbamateYield 14.1%

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-(3-phenyl-1H-1,2,4-triazol-1-yl)propionoic acid (195 mg, 862 μmol), diphenyl phosphorazidate (242 μl, 1.12 mmol), triethylamine (240 μl, 1.72 mmol) in ter-butanol (33 mL) was heated at 50° C. for 5 h. Stirring was continued at 90° C. for another 12 h and all volatiles were removed in vacuo. The crude product was purified by preparative HPLC using an acetonitrile/water (containing 0.1% formic acid) gradient to afford the product as colorless oil (37 mg, 122 μmol, 14.1%). MS: M=289.1 (M+H)+

Workup

customall volatiles were removed in vacuo
customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-b7719a457e294df7afa9db850c98cf18
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772510B2

Reaction notes

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