HCID 14581286, compound → HCID 14581288, compound

HRID 1194088Notes

Reaction equation

HRID 1194088 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:18])[C@@H:12]2[N:15]([CH3:17])[CH3:16])[C:9]=1[C:19]([O:21]CC1C=CC([N+]([O-])=O)=CC=1)=[O:20])(=[O:3])[CH3:2]>O1CCCC1.P([O-])([O-])([O-])=O.[Pt]=O>[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:18])[C@@H:12]2[N:15]([CH3:16])[CH3:17])[C:9]=1[C:19]([OH:21])=[O:20])(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 14581286HCID 14581286, compound

Product 1

HCID 14581288HCID 14581288, compoundYield 7.1%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 1061PhosphateSolventHCID 8028TetrahydrofuranSolvent

Procedure

Forty milligrams (0.09 mmol) of p-nitrobenzyl (5R,6R)-3-(2-acetamidoethyl)thio-6-dimethylamino-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate [35] was dissolved in 5 ml of tetrahydrofuran and 2 ml of 0.01M phosphate buffer (pH 7.2), and catalystically reduced in the presence of 50 mg of platinum oxide at room temperature under 4 atmosphere for 3 hours. The reaction mixture was filtered, and concentrated under reduced pressure. The filtrate and the washing were combined, and sodium chloride was added to a concentration of 5%. The solution was adsorbed on a column of CHP-20 (20 ml). The column was eluted with deionized water. Those fractions in the eluates which showed a UV absorption at 307 nm were lyophilized to give 2 mg of the captioned compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. additionsodium chloride was added to a concentration of 5%
  4. washThe column was eluted with deionized water
  5. customa UV absorption at 307 nm

Sources & evidence

ORD record
ord-4c6da1685df64ca792dd568a7df25b25
Source dataset
uspto-grants-1989_03
Patent number
US04812563

Reaction notes

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