Triethylamine → HCID 56770463, compound

HRID 221341Notes

Reaction equation

HRID 221341 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.O[NH:29][C:30](=[NH:37])[C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[O:12][N:37]=[C:30]([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)[N:29]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 178513374HCID 178513374, compound

Product 1

HCID 56770463HCID 56770463, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tert-butoxycarbonylaminoacetic acid (11.0 g, 5.71 mmol) and triethylamine (802 μl, 5.71 mmol) in toluene (30 ml) was cooled to 0° C. and isobutylchloroformate (740 μl, 5.71 mmol) introduced dropwise. The reaction mixture was stirred at 0° C. for 10 min and at rt for 30 min, whereupon N-hydroxyisonicotinamidine (652 mg, 4.76 mmol) and powdered 3 Å molecular sieves (4 g) were added. After heating under reflux for 12 h the reaction was cooled, filtered through celite and the solvent removed in vacuo. The residue was dissolved in EtOAc (200 ml) and washed with water (30 ml) and saturated aqueous NaHCO3 (30 ml), then dried (MgSO4). The solvent was removed and the residue purified by flash chromatography (IH-EtOAc, 2:3) to afford the title compound: RT=2.97 min; m/z (ES+)=277.1 [M+H]+.

Workup

  1. additionwere added
  2. temperatureAfter heating
  3. temperatureunder reflux for 12 h the reaction
  4. temperaturewas cooled
  5. filtrationfiltered through celite
  6. customthe solvent removed in vacuo
  7. dissolutionThe residue was dissolved in EtOAc (200 ml)
  8. washwashed with water (30 ml) and saturated aqueous NaHCO3 (30 ml)
  9. dry with materialdried (MgSO4)
  10. customThe solvent was removed
  11. customthe residue purified by flash chromatography (IH-EtOAc, 2:3)

Sources & evidence

ORD record
ord-5a03f2013d8c40c8b797721547c2b1cb
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

Loading…