Water → 6-Aminopenicillanic acid

HRID 267184

Reaction equation

HRID 267184 reaction equation
C1C=CC(CC(NC2C=CC([N+]([O-])=O)=C(C(O)=O)C=2)=O)=CC=1.[CH3:23][C:24]1([CH3:46])[S:28][C@@H:27]2[C@H:29]([NH:32]C(COC3C=CC=CC=3)=O)[C:30](=[O:31])[N:26]2[C@H:25]1[C:43]([O-:45])=[O:44].[K+].O>C(N(CC)CC)C>[CH3:23][C:24]1([CH3:46])[S:28][C@@H:27]2[C@H:29]([NH2:32])[C:30](=[O:31])[N:26]2[C@H:25]1[C:43]([OH:45])=[O:44]

Participants

5

Reactant 3

HCID 962WaterHCID 1938646-Nitro-3-phenylacetamidobenzoic acidHCID 23676814Penicillin V Potassium

Product 1

HCID 110826-Aminopenicillanic acidYield 86.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
38 °C

Procedure

290 g of carrier-bound penicillinacylase according to Example 4, having an enzymatic activity of 2,803 U (NIPAB test) and 138 g of potassium penicillin V are added to 2,000 ml of water and stirred for 9 hours at 38°C. The pH value is kept constant at 7.8 by continuous addition of triethylamine. The mixture is worked up as described in Example 1. Yields of 6-APA 64.3 g (86.1% of theory); purity 97.4%.

Sources & evidence

ORD record
ord-b637f9b0888d47a1a842be6a33c686f8
Source dataset
uspto-grants-1976_03
Patent number
US03941756

Linked notes

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