Hydrochloric Acid → HCID 131710055, compound

HRID 972711Notes

Reaction equation

HRID 972711 reaction equation
C([NH:20][CH:21]1[C:38](=[O:39])[N:23]2[C:24]([C:31]([O:33]C(C)(C)C)=[O:32])=[C:25]([CH:28]([CH3:30])[CH3:29])[CH2:26][S:27][C@H:22]12)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>[N+](C)([O-])=O>[NH2:20][C@H:21]1[C:38](=[O:39])[N:23]2[C:24]([C:31]([OH:33])=[O:32])=[C:25]([CH:28]([CH3:30])[CH3:29])[CH2:26][S:27][C@H:22]12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131710056HCID 131710056, compound

Product 1

HCID 131710055HCID 131710055, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A mixture of 541 mg of tert.butyl 7-tritylamino-3-isopropyl-3-cepheme-4-carboxylate in 11 ml of nitromethane was cooled on an ice bath and a current of gaseous hydrochloric acid was passed therethrough for 15 minutes. The mixture was evaporated to dryness and the residue was taken up in ether. The ether solution was vacuum filtered and the residue was washed with ether and dried. The residue was taken up in 1 ml of water and the pH was adjusted to 4 by addition of pyridine. The mixture was vacuum filtered and the crystals were washed with water, with acetone and then with ether and dried to obtain 204 mg of dl cis 7-amino-3-isopropyl-3-cepheme-4-carboxylic acid in the form of colorless crystals melting towards 230° C. with decomposition.

Workup

  1. temperaturewas cooled on an ice bath
  2. customThe mixture was evaporated to dryness
  3. filtrationfiltered
  4. washthe residue was washed with ether
  5. customdried
  6. additionthe pH was adjusted to 4 by addition of pyridine
  7. filtrationfiltered
  8. washthe crystals were washed with water, with acetone
  9. dry with materialwith ether and dried

Sources & evidence

ORD record
ord-3091f63559824271b4fb3f4580bd8d27
Source dataset
uspto-grants-1977_10
Patent number
US04053597

Reaction notes

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