Potassium → 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, 4-oxide

HRID 904060Notes

Reaction equation

HRID 904060 reaction equation
[K].O(CC(NC1C(=O)N2C(C(O)=O)C(C)(C)S[C@H]12)=O)C1C=CC=CC=1.OO[S:28]([O-:30])=O.[K+].[CH3:32][C:33]1([CH3:54])S[C@@H:36]2[C@H:38]([NH:41][C:42]([CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[O:43])[C:39](=[O:40])[N:35]2[C@H:34]1[C:51]([O-:53])=[O:52].[K+]>O>[CH3:32][C:33]1([CH3:54])[S:28](=[O:30])[C@@H:36]2[C@H:38]([NH:41][C:42]([CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[O:43])[C:39](=[O:40])[N:35]2[C@H:34]1[C:51]([OH:53])=[O:52]

Participants

6

Reactant 4

HCID 5462222PotassiumHCID 123738936-(2-Phenoxyacetamido)-2,2-dimethylpenam-3-carboxylic acidHCID 23664709Penicillin G PotassiumHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 1074964-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, 4-oxideYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 50 ml. of water were added 19.4 grams (50 millimoles) of the potassium salt of 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylic acid. A solution of 20 grams (65 millimoles active oxygen) of Oxone® in 100 ml. water was added dropwise to the penicillin solution over a 45 minute period. The mixture was stirred for about 10 minutes at room temperature. The resulting precipitate was collected by filtration and washed with 25 ml. of water. The precipitate was dried in vacuo at 40° C. overnight to afford 17.95 grams (98%) of the corresponding penicillin sulfoxide. Analysis of the product by high performance liquid chromatography (HPLC) indicated the presence of 23.0% of the α-isomer and 74.1% of the β-isomer.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with 25 ml
  3. customThe precipitate was dried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-650932ad34d041a6a44cbf34afdc1dbf
Source dataset
uspto-grants-1980_10
Patent number
US04230620

Reaction notes

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