Reaktion #1920591

ord-b18adc18aa7e45aa8288d8e5b0b1dbda

Reaktionsgleichung

CC1(C)OC(=O)C(c2ccccc2)C(=O)O1
2.2-dimethyl-5-phenyl-1.3-dioxane-4.6-dione
CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O
6-aminopenicillanic acid
→
CC1(C)S[C@@H]2[C@H](NC(=O)C(C(=O)O)c3ccccc3)C(=O)N2[C@H]1C(=O)O
6-(α-carboxy-α-phenylacetamido)penicillanic acid
CC1(C)S[C@@H]2[C@H](NC(=O)C(C(=O)O)c3ccccc3)C(=O)N2[C@H]1C(=O)O
carbenicillin

Edukte

—
2.2-tetramethylene-5-phenyl-1.3-dioxane-4.6-dione
CC1(C)OC(=O)C(c2ccccc2)C(=O)O1
2.2-dimethyl-5-phenyl-1.3-dioxane-4.6-dione
CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O
6-aminopenicillanic acid

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

When an equivalent amount of 2.2-tetramethylene-5-phenyl-1.3-dioxane-4.6-dione prepared in the example 3 is substituted for 2.2-dimethyl-5-phenyl-1.3-dioxane-4.6-dione and the reaction with 6-aminopenicillanic acid is carried out as disclosed in the example 1, 6-(α-carboxy-α-phenylacetamido)penicillanic acid (carbenicillin) is obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04066664uspto-grants-1978_01