HCID 14230815, compound → HCID 14230821, compound

HRID 1759233Notes

Reaction equation

HRID 1759233 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15]([S:16][C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[N:14]([CH:25]([N:36]=[N+]=[N-])[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C:13]1=[O:39])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)=O>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15]([S:16][C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[N:14]([CH:25]([NH2:36])[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C:13]1=[O:39])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 14230815HCID 14230815, compound

Product 1

HCID 14230821HCID 14230821, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 284Formic AcidSolvent2×

Procedure

A mixture of benzyl 2-[3-phenoxyacetamido-4-(2,2,2-trichloroethoxycarbonylthio)-2-oxo-1-azetidinyl]-2-azidoacetate (2.856 g.) and 10% palladium on carbon (600 mg.) in formic acid (27 ml.) was stirred at room temperature under hydrogen atmosphere. After stirring for an hour, to the mixture was added 5% palladium on carbon (600 mg.) in formic acid (8 ml.) and stirred under hydrogen atmosphere for additional 2.5 hours. The resultant mixture was filtered through a pad of Celite and the filter cake was washed with methylene chloride. The filtrate and washings were combined and concentrated in vacuo to a volume of 15 ml. A part of this concentrate was evaporated to dryness to give benzyl 2-[3-phenoxyacetamido-4-(2,2,2-trichloroethoxycarbonylthio)-2-oxo-1-azetidinyl]-2-aminoacetate.

Workup

  1. stirringAfter stirring for an hour, to the mixture
  2. stirringstirred under hydrogen atmosphere for additional 2.5 hours
  3. filtrationThe resultant mixture was filtered through a pad of Celite
  4. washthe filter cake was washed with methylene chloride
  5. concentrationconcentrated in vacuo to a volume of 15 ml
  6. customA part of this concentrate was evaporated to dryness

Sources & evidence

ORD record
ord-d09159d5a75246ffa09df42372efeacf
Source dataset
uspto-grants-1982_07
Patent number
US04339449

Reaction notes

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