Hydrogen Peroxide → 6-[(1-Hydroxy-2-phenoxyethylidene)amino]-3,3-dimethyl-4,7-dioxo-4lambda~4~-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

HRID 1736270Notes

Reaction equation

HRID 1736270 reaction equation
C(O)(=[O:15])CCCCCCCCCCCCC.OO.[CH3:19][C:20]1([CH3:42])[S:24][C@@H:23]2[C@H:25]([NH:28][C:29]([CH2:31][O:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:30])[C:26](=[O:27])[N:22]2[C@H:21]1[C:39]([OH:41])=[O:40].[K].P([O-])([O-])([O-])=O>C1(C)C=CC=CC=1.C(#N)C>[CH3:19][C:20]1([CH3:42])[S:24](=[O:15])[C@@H:23]2[C@H:25]([NH:28][C:29]([CH2:31][O:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:30])[C:26](=[O:27])[N:22]2[C@H:21]1[C:39]([OH:41])=[O:40]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1061PhosphateHCID 11005Myristic AcidHCID 9865150132-98-9

Product 1

HCID 1076026-[(1-Hydroxy-2-phenoxyethylidene)amino]-3,3-dimethyl-4,7-dioxo-4lambda~4~-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To a mechanically stirred suspension of immobilized C. antarctica lipase (150 mg, according to example 1) in toluene (15 ml) and myristic acid (1 g, 4.6 mmol), was hydrogen peroxide (1.2 ml 60% (w/v), 21 mmol in all) added in four equal portions after 0, 2, 3 and 4 hours. Penicillin V-potassium salt (2.4 g, 6.2 mmol in all) was added in three equal portions after 2, 3 and 4 hours. The yields were determined by HPLC (Column: Supelco RP-18, 5 micro; Mobile phase: Acetonitrile 20% and pH 6.5 Phosphate buffer 80%; Flow: 1 ml/min. UV-detector). Full turnover was reached after 5 hours total reaction time.

Workup

  1. additionTo a mechanically stirred suspension of immobilized C
  2. additionadded in four equal portions after 0, 2, 3 and 4 hours

Sources & evidence

ORD record
ord-e448e98d2ef349efae27b5d552dc70ee
Source dataset
uspto-grants-1996_07
Patent number
US05541092

Reaction notes

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