Hydrochloric Acid → 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 904993Notes

Reaction equation

HRID 904993 reaction equation
[CH3:1][C:2]1([CH3:23])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([OH:22])=[O:21].[K].I([O-])(=O)(=O)=[O:26].[Na+].Cl>O.ClCCl>[CH3:1][C:2]1([CH3:23])[S:6](=[O:26])[C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([OH:22])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5904Penicillin GHCID 5462222PotassiumHCID 23667635Sodium periodate

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-oxide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Penicillin G, potassium salt (349.9 g) was dissolved in 3 liters of water. Sodium periodate (194 g) was added and the mixture was stirred for three hours. Dichloromethane (500 ml) was added and the pH of the water layer was adjusted to 2.3 with 6 N hydrochloric acid with vigorous stirring. The aqueous layer was separated and extracted with four 400 ml portions of dichloromethane. The combined extract was washed with aqueous sodium bisulfite to remove any iodine color, dried over sodium sulfate, filtered, and evaporated. The solid residue was empasted with 400 ml of ethyl acetate and allowed to stand at 0° C. overnight. The solid was isolated by filtration and dried in vacuo to afford 322 g of penicillin G sulfoxide.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with four 400 ml portions of dichloromethane
  3. extractionThe combined extract
  4. washwas washed with aqueous sodium bisulfite
  5. customto remove any iodine color
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. waitto stand at 0° C. overnight
  10. customThe solid was isolated by filtration
  11. customdried in vacuo

Sources & evidence

ORD record
ord-4925af44f18e475b93b44f5a54fba248
Source dataset
uspto-grants-1983_12
Patent number
US04421686

Reaction notes

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