Acetic Acid → HCID 22812922, compound

HRID 224549Notes

Reaction equation

HRID 224549 reaction equation
[CH2:1]([O:5][C@H:6]1[N:9]([C:10](=[O:27])[C:11]([O:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:8](=[O:28])[C@@H:7]1[NH:29][C:30](=[O:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:2]([CH3:4])=[O:3].C(O)(=O)C>C(Cl)Cl.[Zn]>[CH2:1]([O:5][C@H:6]1[N:9]([CH:10]([OH:27])[C:11]([O:13][CH:14]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:8](=[O:28])[C@@H:7]1[NH:29][C:30](=[O:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22812923HCID 22812923, compound

Product 1

HCID 22812922HCID 22812922, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of diphenylmethyl α-[4(R)-acetonyloxy-3(R)-phenylacetamido-2-oxo-azetidin-1-yl]glyoxalate (2.312 g) in a mixture of methylene chloride (10 ml) and glacial acetic acid (10 ml) is added activated zinc powder (2.50 g) with stirring, and the mixture is stirred for 3 hours at room temperature. The reaction mixture is filtered through a layer of Celite which is washed with methylene chloride. The filtrate is washed with water, dried over sodium sulfate, and evaporated under reduced pressure to give the product as a mixture of epimers at position α.

Workup

  1. additionis added
  2. stirringthe mixture is stirred for 3 hours at room temperature
  3. filtrationThe reaction mixture is filtered through a layer of Celite which
  4. washis washed with methylene chloride
  5. washThe filtrate is washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customto give the product
  9. additionas a mixture of epimers at position α

Sources & evidence

ORD record
ord-4efa16f399c04383b81965e829df1f74
Source dataset
uspto-grants-1980_11
Patent number
US04233216

Reaction notes

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