Hydrochloric Acid → (6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1415413Notes

Reaction equation

HRID 1415413 reaction equation
NN.Cl.[NH2:4][CH:5]1[C:16](=[O:17])[N:7]2[C:8]([C:13]([O-:15])=[O:14])=[C:9]([CH3:12])[CH2:10][S:11][C@H:6]12.CC1CS[C@@H]2[C@H](N)C(=O)N2C=1C(O)=O>O1CCCC1.O>[NH2:4][CH:5]1[C:16](=[O:17])[N:7]2[C:8]([C:13]([OH:15])=[O:14])=[C:9]([CH3:12])[CH2:10][S:11][C@H:6]12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 334987-Aminodeacetoxycephalosporanic acidHCID 131710627HCID 131710627, compound

Product 1

HCID 13475828(6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 7-phthalisoimido-3-methyl-3-cephem-4-carboxylate (172 mg., 0.5 mmol.) in tetrahydrofuran (7 ml.) at 0° was added anhydrous hydrazine (.032 ml., 1 mmol.). After 7 min., 1N HCl (2.5 ml.) and water (2.5 ml.) were added. The mixture was heated on a stream bath for 10 min. after which it was cooled and evaporated in vacuo to a volume of ca. 5 ml. The aqueous solution was filtered, and the pH of the filtrate was adjusted to 3.7 with 5% sodium bicarbonate solution. After 15 min. the solution was filtered giving 73 mg. (68%) of 7-amino-3-methyl-3-cephem-4-carboxylate. Spectral data as well as tlc data showed the product to be identical with an authentic sample of 7-ADCA.

Workup

  1. temperatureThe mixture was heated on a stream bath for 10 min. after which it
  2. temperaturewas cooled
  3. customevaporated in vacuo to a volume of ca. 5 ml
  4. filtrationThe aqueous solution was filtered
  5. filtrationAfter 15 min. the solution was filtered
  6. customgiving 73 mg

Sources & evidence

ORD record
ord-9303885d2ea2494fbbe9a09237956629
Source dataset
uspto-grants-1977_01
Patent number
US04005074

Reaction notes

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