Acetic Acid → HCID 86743480, compound

HRID 892636Notes

Reaction equation

HRID 892636 reaction equation
CCCC[CH2:5][CH3:6].C([Li])CCC.C1[CH2:16][O:15][CH2:14]C1.[CH2:17]1[C@@H:21]2[CH2:22][C:23](=[O:24])[N:20]2[CH2:19][CH2:18]1.C(O)(=[O:27])C>CO>[CH3:14][O:15][C:16]([CH:19]1[N:20]2[C:23](=[O:24])[CH:22]([CH2:5][CH3:6])[C@H:21]2[CH2:17][CH2:18]1)=[O:27]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 67790551HCID 67790551, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 86743480HCID 86743480, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an anhydrous THF solution (3 ml) of LDA, as produced from diisopropylamine (0.03 ml, 0.19 mmol) and a 15% n-butyllithium hexane solution (0.12 ml, 0.19 mmol), anhydrous THF solution (2 ml) of the carbapenam (VI) (16 mg, 0.08 mmol) was added dropwise at -78° C. under a carbapenam (VI) (16 mg, 0.08 mmol) was added dropwise at -78° C. under a current of argon. The mixture was stirred for 30 minutes and a mixture of acetic acid and methanol (1:1, v/v) (0.5 ml) was added. It was warmed to room temperature and extracted with ether. The ether layer was washed with water and dried with anhydrous magnesium sulfate. The solvent was distilled off and the thus obtained residue was subjected to HPLC purification. A fraction eluting with a mixture of n-hexane and ethyl acetate (9:1, v/v) gave a mixture (12 mg) of a carbapenam in the 5,6-cis form (IX) with a small quantity of by-product.

Workup

  1. additionwas added dropwise at -78° C. under a current of argon
  2. additionv/v) (0.5 ml) was added
  3. extractionextracted with ether
  4. washThe ether layer was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe thus obtained residue was subjected to HPLC purification
  8. washA fraction eluting with a mixture of n-hexane and ethyl acetate (9:1

Sources & evidence

ORD record
ord-1cdba9fe42024fc0b457f2e776311eeb
Source dataset
uspto-grants-1992_06
Patent number
US05118831

Reaction notes

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