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

HRID 267183

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

120 g of carrier-bound penicillinacylase (moist weight) according to Example 4, with an activity of 1,160 U (NIPAB test) and 120 g of potassium penicillin G, are introduced into 1,300 ml of water and stirred for 9 hours at 38°C. and pH 7.8, as described in Example 14. The mixture is worked up as described in Example 14. The carrier-bound penicillinacylase is employed 5 times in succession for the enzymatic splitting reaction. The yields of 6-APS achieved are listed below:

Workup

customfor the enzymatic splitting reaction

Sources & evidence

ORD record: ord-741bdb9948c84a0cb32c17c4d75c97b1
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03941756

Linked notes

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