6-Nitro-3-phenylacetamidobenzoic acid → 6-Aminopenicillanic acid

HRID 267182

Reaction equation

C1C=CC(CC(NC2C=CC([N+]([O-])=O)=C(C(O)=O)C=2)=O)=CC=1.[CH3:23][C:24]1([CH3:45])[S:28][C@@H:27]2[C@H:29]([NH:32]C(CC3C=CC=CC=3)=O)[C:30](=[O:31])[N:26]2[C@H:25]1[C:42]([O-:44])=[O:43].[K+]>O>[CH3:23][C:24]1([CH3:45])[S:28][C@@H:27]2[C@H:29]([NH2:32])[C:30](=[O:31])[N:26]2[C@H:25]1[C:42]([OH:44])=[O:43]

Participants

Conditions

Temperature: 38 °C

Procedure

330 g of carrier-bound penicillinacylase produced according to Example 1, having an enzymatic activity of 3,410 U (NIPAB test) and 129 g of potassium penicillin G are successively added to 2,000 ml of water and stirred at 38°C. and pH 7.8 as described in Example 14. The penicillin G is completely split to 6-APA and phenylacetic acid over the course of 2 hours. The 6-APA is isolated as described in Example 14. The carrierbound penicillinacylase is employed 20 times in succession. Even after the twentieth splitting, the reaction time does not have to be extended to achieve complete splitting.

Workup

custom330 g of carrier-bound penicillinacylase produced
customThe penicillin G is completely split to 6-APA and phenylacetic acid over the course of 2 hours

Sources & evidence

ORD record: ord-4b6ddb4097a74bda95fdc984c65e90cf
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03941756

Linked notes

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