Hydrochloric Acid → HCID 131710055, compound

HRID 1657715Notes

Reaction equation

HRID 1657715 reaction equation
Cl.C([NH:21][C@H:22]1[C:35](=[O:36])[N:24]2[C:25]([C:32]([O-:34])=[O:33])=[C:26]([CH:29]([CH3:31])[CH3:30])[CH2:27][S:28][C@H:23]12)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N+](C)([O-])=O>[NH2:21][C@H:22]1[C:35](=[O:36])[N:24]2[C:25]([C:32]([OH:34])=[O:33])=[C:26]([CH:29]([CH3:31])[CH3:30])[CH2:27][S:28][C@H:23]12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131710301HCID 131710301, compound

Product 1

HCID 131710055HCID 131710055, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A current of gaseous hydrogen chloride was passed for 15 minutes through a mixture of 541 mg of tert.-butyl DL cis 7-tritylamino-3-isopropyl-3-cepheme-4-carboxylate in 11 ml of nitromethane on an ice bath and the mixture was then evaporated to dryness. The residue was taken in ether and was vacuum filtered. The precipitate was washed with ether, dried and dissolved in 1 ml of water. The pH was adjusted to 4 with pyridine addition and the mixture was vacuum filtered. The crystals recovered were washed with water, then acetone and ether and dried to obtain 204mg of DL cis 7-amino-3-isopropyl-3-cepheme-4-carboxylic acid melting at 230°C with decomposition. The product occurred as colorless crystals slightly soluble in water, ethanol and acetone and insoluble in ether.

Workup

  1. customthe mixture was then evaporated to dryness
  2. filtrationfiltered
  3. washThe precipitate was washed with ether
  4. customdried
  5. dissolutiondissolved in 1 ml of water
  6. additionThe pH was adjusted to 4 with pyridine addition
  7. filtrationfiltered
  8. customThe crystals recovered
  9. washwere washed with water
  10. dry with materialacetone and ether and dried

Sources & evidence

ORD record
ord-3b657fe1071146b7b387e9887726c1cf
Source dataset
uspto-grants-1976_06
Patent number
US03962223

Reaction notes

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