Di-tert-butyl oxalate → HCID 54691687, compound

HRID 1034218Notes

Reaction equation

HRID 1034218 reaction equation
[C:1]1([NH:7][CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](OC(C)(C)C)(=[O:25])[C:18](OC(C)(C)C)=[O:19].CC(C)([O-])C.[K+]>C1COCC1>[OH:25][C:17]1[C:18](=[O:19])[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][C:9]=1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 69651Di-tert-butyl oxalateHCID 22121642HCID 22121642, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54691687HCID 54691687, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title compound of Example B (29.37 g, 0.133 mol) and di-tert-butyl oxalate (26.90 g, 0.133 mol) in dry THF (350 ml) was added potassium tert-butoxide (29.84 g, 0.266 mol) and the resulting solution was heated under reflux for 24 h. The mixture was then cooled and the solvent removed in vacuo. The resulting solid was suspended in CH2Cl2 and 1N aqueous HCl was added. The resulting suspension was filtered and the organic filtrate was dried over MgSO4 and concentrated in vacuo. The residue was then chromatographed on silica gel eluting with 1/1/98 HOAc/EtOH/CH2Cl2 to give the title compound (19.06 g, 52%) as a solid. Anal calcd for C15H17NO4 : C, 65.44; H, 6.22; N, 5.09. Found: C, 65.05; H, 6.33; N, 4.86. MS M+1 calcd for C15H17NO4 276, found 276.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 24 h
  3. temperatureThe mixture was then cooled
  4. customthe solvent removed in vacuo
  5. addition1N aqueous HCl was added
  6. filtrationThe resulting suspension was filtered
  7. dry with materialthe organic filtrate was dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was then chromatographed on silica gel eluting with 1/1/98 HOAc/EtOH/CH2Cl2

Sources & evidence

ORD record
ord-e9d88ec21ab84c74815798e0fe7fb384
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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