Chloroform → HCID 70507499, compound

HRID 2296554Notes

Reaction equation

HRID 2296554 reaction equation
[C:1]([O:4][CH:5]1[C@@H:9]2[CH2:10][C:11](=[O:12])[N:8]2[CH:7]([C:13]([O:15]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:14])[CH:6]1[CH3:29])(=[O:3])[CH3:2].C(Cl)(Cl)Cl>[Pd].C(OCC)(=O)C>[C:1]([O:4][CH:5]1[C@@H:9]2[CH2:10][C:11](=[O:12])[N:8]2[CH:7]([C:13]([OH:15])=[O:14])[CH:6]1[CH3:29])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 70509313HCID 70509313, compound

Product 1

HCID 70507499HCID 70507499, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

Benzhydryl 1-acetoxy-2-methylcarbapenam-3-carboxylate (26 mg.) was dissolved in 3 ml. of ethyl acetate. Hydrogenation catalyst (10% palladium on carbon, 26 mg.) was added and the reaction mixture hydrogenated at room temperature and atmospheric pressure for 1 hour, at which time tlc (4:1 chloroform:ethyl acetate) indicated no starting material remained. The catalyst was recovered by filtration and the filtrate evaporated in vacuo to yield 1-acetoxy-2-methylcarbapenam-3-carboxylic acid [15 mg.; Rf 0.0 (4:1 chloroform:ethyl acetate); ir (CH2Cl2) 1770, 1730 cm-1 ].

Workup

  1. filtrationThe catalyst was recovered by filtration
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-50e149c6d5c749b8aa50549ff8eb72a3
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

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