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Hydrogen Peroxide → 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((2-phenoxyacetyl)amino)-, 4-oxide, (2S,5R,6R)-

HRID 1736270
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1061PhosphateHCID 11005Myristic AcidHCID 98651504-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-, potassium salt (1:1), (2S,5R,6R)-

Product 1

HCID 1076024-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((2-phenoxyacetyl)amino)-, 4-oxide, (2S,5R,6R)-

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05541092

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes