Reaktion #445615

ord-433695d9204e48309c42fc99dc140bbc

Reaktionsgleichung

CC1(C)S[C@H]2N(C(=O)C2(Br)Br)[C@H]1C(=O)O
6,6-dibromopenicillanic acid
→
CC1(C)S[C@@H]2CC(=O)N2[C@H]1C(=O)O
penicillanic acid
CC1(C)S[C@H]2N(C(=O)C2(Br)Br)[C@H]1C(=O)O
6,6-dibromopenicillanic acid

Edukte

CC1(C)S[C@H]2N(C(=O)C2(Br)Br)[C@H]1C(=O)O
6,6-dibromopenicillanic acid
—
( C )

Reagenzien

[Pd]
Pd/C
O=C([O-])[O-].[Ca+2].[Pd]
Pd CaCO3

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeto produce
  2. 2
    workup.ADDITIONa mixture of 6-alpha- and 6-beta-bromopenicillanic acid
  3. 3
    Sonstigeto produce methyl 6-alpha-bromopenicillanate and methyl penicillanate

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04468351uspto-grants-1984_08