Chloroform → HCID 70507140, compound

HRID 2296562Notes

Reaction equation

HRID 2296562 reaction equation
[C:1]([O:4][CH:5]1[C@@H:9]2[CH:10]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11](=[O:12])[N:8]2[CH:7]([C:24]([O:26]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:25])[CH:6]1[CH3:40])(=[O:3])[CH3:2].C(Cl)(Cl)Cl>[Pd].C(OCC)(=O)C>[C:1]([O:4][CH:5]1[C@@H:9]2[CH:10]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11](=[O:12])[N:8]2[CH:7]([C:24]([OH:26])=[O:25])[CH:6]1[CH3:40])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 70507631HCID 70507631, compound

Product 1

HCID 70507140HCID 70507140, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

Benzhydryl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate (18 mg.) was dissolved in 3 ml. of ethyl acetate. Hydrogenation catalyst (18 mg. of 10% palladium on carbon) was added and the mixture hydrogenated at atmospheric pressure and room temperature for 1 hour. When tlc (4:1 chloroform:ethyl acetate) indicated no change, a second aliquot of catalyst (18 mg.) was added. According to tlc assay, some conversion occurred during the next hour, at which time a third aliquot of catalyst (18 mg.) was added. At the end of another hour of hydrogenation, tlc assay indicated reduction to be complete. Catalyst was recovered by filtration with ethyl acetate wash. The combined filtrate and washes were evaporated to dryness in vacuo to yield 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylic acid [Rf 0.77 (18:1 acetone:water); ir (CH2Cl2) 1775, 1725, 1675 cm-1 ].

Workup

  1. additiona second aliquot of catalyst (18 mg.) was added
  2. additionwas added
  3. filtrationCatalyst was recovered by filtration with ethyl acetate
  4. washwash
  5. customThe combined filtrate and washes were evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-3765791af2fd4499b9b8cc9d44ee9c55
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

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