6,6-Dibromopenicillanic acid → Penicillanic Acid

HRID 358433

Reaction equation

HRID 358433 reaction equation
[CH3:1][C:2]1([CH3:15])[S:6][C@@H:5]2[C:7]([Br:11])([Br:10])[C:8](=[O:9])[N:4]2[C@H:3]1[C:12]([OH:14])=[O:13]>[Pd].[Pd].C([O-])([O-])=O.[Ca+2]>[CH3:1][C:2]1([CH3:15])[S:6][C@@H:5]2[C:7]([Br:11])([Br:10])[C:8](=[O:9])[N:4]2[C@H:3]1[C:12]([OH:14])=[O:13].[CH3:1][C:2]1([CH3:15])[S:6][C@@H:5]2[CH2:7][C:8](=[O:9])[N:4]2[C@H:3]1[C:12]([OH:14])=[O:13]

Participants

5

Reactant 1

HCID 903766,6-Dibromopenicillanic acid

Product 2

HCID 6891Penicillanic AcidHCID 903766,6-Dibromopenicillanic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 12000666Calcium Palladium CarbonateCatalyst

Procedure

Pratt, U.S. Pat. No. 4,180,506, describes catalytic hydrogenation of 6,6-dibromopenicillanic acid over Pd/C catalyst to produce a mixture of 6-alpha- and 6-beta-bromopenicillanic acid. Clayton, J. Chem. Soc. (C), pp. 2123-2127 (1969), describes the hydrogenation of methyl 6,6-dibromopenicillanate over Pd/CaCO3 to produce methyl 6-alpha-bromopenicillanate and methyl penicillanate; and hydrogenation of 6,6-dibromopenicillanic acid over the same catalyst to produce penicillanic acid.

Workup

  1. customto produce
  2. additiona mixture of 6-alpha- and 6-beta-bromopenicillanic acid
  3. customto produce methyl 6-alpha-bromopenicillanate and methyl penicillanate

Sources & evidence

ORD record
ord-433695d9204e48309c42fc99dc140bbc
Source dataset
uspto-grants-1984_08
Patent number
US04468351

Linked notes

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