tert-Butanol → HCID 58415444, compound

HRID 46169Notes

Reaction equation

HRID 46169 reaction equation
FC(F)(F)[C:3]([O-:5])=[O:4].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([CH2:27]C(O)=O)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]3=[NH+:24][CH:25]=[CH:26][N:16]23)=[CH:11][CH:10]=1.CC[N:33](CC)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:55][C:56](O)([CH3:58])[CH3:57]>>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2([CH2:27][NH:33][C:3](=[O:4])[O:5][C:56]([CH3:58])([CH3:57])[CH3:55])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]3=[N:24][CH:25]=[CH:26][N:16]23)=[CH:13][CH:14]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 1785249895-(4-bromophenyl)-5-(carboxymethyl)-5H-imidazo[2,1-a]isoindol-1-ium trifluoroacetate

Product 1

HCID 58415444HCID 58415444, compound

Procedure

A mixture of 5-(4-bromophenyl)-5-(carboxymethyl)-5H-imidazo[2,1-a]isoindol-1-ium trifluoroacetate (1.27 g), Et3N (0.989 mL) and 4 Angstrom powdered molecular sieves in t-BuOH (10 mL) was stirred for 20 minutes at room temperature. Diphenylphosphorylazide was then added to this mixture and heated at 95° C. overnight. After cooling to room temperature the reaction mixture was filtered through a pad of celite. The celite pad was washed thoroughly with CH2Cl2, combined washings and filtrate were concentrated. The residue was dissolved in CH2Cl2 and the organic layer was washed with half-saturated aqueous NaHCO3 solution (1×), dried over Na2SO4 and concentrated. Flash chromatography using a linear gradient of 3% EtOAc/0% MeOH to 50% EtOAc/2% MeOH in hexanes afforded title compound as a white solid. Mass. found (M+H)+, 442.0.

Workup

  1. temperatureheated at 95° C. overnight
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. filtrationwas filtered through a pad of celite
  4. washThe celite pad was washed thoroughly with CH2Cl2
  5. concentrationwere concentrated
  6. dissolutionThe residue was dissolved in CH2Cl2
  7. washthe organic layer was washed with half-saturated aqueous NaHCO3 solution (1×)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b1ca0d1781b8406abf05e8e0d8324b42
Source dataset
uspto-grants-2013_09
Patent number
US08541595B2

Reaction notes

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