3,5-Di-tert-butyl-1,2-benzoquinone → Benzyl-6-oxopenicillanate

HRID 972479Notes

Reaction equation

HRID 972479 reaction equation
[CH3:1][C:2]1([CH3:21])[S:6][C@@H:5]2[CH:7](N)[C:8](=[O:9])[N:4]2[C@H:3]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].C(C1C(=O)C(=[O:36])C=C(C(C)(C)C)C=1)(C)(C)C>O1CCCC1>[CH3:1][C:2]1([CH3:21])[S:6][C@@H:5]2[C:7]([C:8](=[O:9])[N:4]2[C@H:3]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:36]

Participants

4

Reactant 2

HCID 769153,5-Di-tert-butyl-1,2-benzoquinoneHCID 70392468HCID 70392468, compound

Product 1

HCID 12923449Benzyl-6-oxopenicillanate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.06 g. (10 mmol.) of 6-aminopenicillanic acid benzyl ester and 2.20 g. (10 mmol.) of 3,5-di-t-butyl-1,2-benzoquinone in 50 ml. of tetrahydrofuran containing 5 g. of 5A molecular sieves is maintained at 4° for 16 hours. The solution is decanted and treated with 3 g. of oxalic acid in 10 ml. of water. After standing at 4° for 6 hours most of the solvent is removed below ambient temperature and the residue is partitioned between benzene and water. The aqueous phase is extracted with additional benzene and the combined organic phases are dried (MgSO4) and evaporated to dryness to give a residue which is chromatographed on silica gel with benzene-ethyl acetate as eluant to give the title compound.

Workup

  1. customThe solution is decanted
  2. additiontreated with 3 g
  3. customis removed below ambient temperature
  4. customthe residue is partitioned between benzene and water
  5. extractionThe aqueous phase is extracted with additional benzene
  6. dry with materialthe combined organic phases are dried (MgSO4)
  7. customevaporated to dryness
  8. customto give a residue which
  9. customis chromatographed on silica gel with benzene-ethyl acetate as eluant

Sources & evidence

ORD record
ord-20f858f6a2e84e0499855c8317bdd20d
Source dataset
uspto-grants-1977_10
Patent number
US04053468

Reaction notes

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