1-(Azidomethyl)-4-methoxybenzene → HCID 18697745, compound

HRID 2289564Notes

Reaction equation

HRID 2289564 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:23])[C:16]#[C:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:11]([N+:24]([O-:26])=[O:25])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][O:28][C:29]1[CH:38]=[CH:37][C:32]([CH2:33][N:34]=[N+:35]=[N-:36])=[CH:31][CH:30]=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:23])[C:16]2[N:36]=[N:35][N:34]([CH2:33][C:32]3[CH:37]=[CH:38][C:29]([O:28][CH3:27])=[CH:30][CH:31]=3)[C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:11]([N+:24]([O-:26])=[O:25])[CH:10]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 109317671-(Azidomethyl)-4-methoxybenzeneHCID 18697750HCID 18697750, compound

Product 1

HCID 18697745HCID 18697745, compoundYield 132.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 4-(4-t-butoxycarbonylamino-2-nitrophenyl)-4-hydroxy-2-butynoate (693 mg, 1.90 mmol) prepared in the step (a) and 4-methoxybenzylazide (776 mg, 4.76 mmol) were dissolved in toluene (30 ml), and the solution was stirred at 100° C. overnight. The solvent was removed under reduced pressure, and the residue was purified by chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give a 1:1 mixture (1.33 g) of ethyl 4-((4-t-butoxycarbonylamino-2-nitrophenyl)hydroxymethyl)-1-(4-methoxybenzyl)-1,2,3-triazole-5-carboxylate and ethyl 5-((4-t-butoxycarbonylamino-2-nitrophenyl)hydroxymethyl)-1-(4-methoxybenzyl)-1,2,3-triazole-4-carboxylate. This mixture (1.33 g) was dissolved in methylene chloride (30 ml), active manganese dioxide (3.5 g) was added to the solution, and the mixture was stirred for 30 min. Manganese dioxide was filtered off through Celite, the filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give a 1:1 mixture (872 mg, 87%) of ethyl 4-(4-t-butoxycarbonylamino-2-nitrobenzoyl)-1-(4-methoxybenzyl)-1,2,3-triazole-5-carboxylate and ethyl 5-(4-t-butoxycarbonylamino-2-nitrobenzoyl)-1-(4-methoxybenzyl)-1,2,3-triazole-4-carboxylate.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by chromatography on silica gel (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-8b574dd49c4b4a7ca4a5773827d83afb
Source dataset
uspto-grants-2000_07
Patent number
US06093714

Reaction notes

Loading…