2-Naphthol → Penicillin G

HRID 129703

Reaction equation

[CH3:1][C:2]1[CH2:11][S:10][C@@H:5]2[C@H:6]([NH2:9])[C:7](=[O:8])[N:4]2[C:3]=1[C:12]([OH:14])=[O:13].[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)C=C[C:16]=1[OH:25].[OH-].[NH4+]>O>[CH3:11][C:2]1([CH3:1])[S:10][C@@H:5]2[C@H:6]([NH:9][C:16]([CH2:15][C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:25])[C:7](=[O:8])[N:4]2[C@H:3]1[C:12]([OH:14])=[O:13]

Participants

Conditions

Temperature: 25 °C

Procedure

The pH value of a mixture (slurry) of D-PGA.1/2H2SO4 (74.7 g, 0.375 mol), 7-ADCA (21.4 g, 0.10 mol), and 2-naphthol (10.8 g, 0.075 mol, particle size <100 μm) in approximately 300 ml of water was adjusted to 6.7 by addition of 4M ammonium hydroxide. Water was added to 400 ml followed by immobilized E. coli Penicillin G acylase prepared as described above (50 g on dry basis suspended in water to a total of 100 ml), and the mixture was stirred at 25° C.

Workup

customon dry basis

Sources & evidence

ORD record: ord-2576228db0324c0b98d3a4546f045b56
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05470717

Linked notes

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