Penicillamine hydrochloride → Penicillamine

HRID 26577

Reaction equation

HRID 26577 reaction equation
Cl.[NH2:2][C@@H:3]([C:8]([OH:10])=[O:9])[C:4]([SH:7])([CH3:6])[CH3:5]>C(O)C>[NH2:2][C@@H:3]([C:8]([OH:10])=[O:9])[C:4]([SH:7])([CH3:6])[CH3:5]

Participants

3

Reactant 1

HCID 92173Penicillamine hydrochloride

Product 1

HCID 5852Penicillamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.50 g (0.02 mole) of o-amino-thiophenol and 8.84 g (0.02 mole) of benzylpenicilloic acid α-benzylamide were added to a solution of 0.73 g (0.02 mole) of concentrated hydrochloric acid in 50 ml of water. The mixture was heated under reflux, with stirring, for 2 hours in a nitrogen atmosphere. After the completion of the reaction, the resulting mixture was allowed to stand at room temperature for an hour. The crystals which formed were separated by filtration, washed with a small amount of water and discarded. The filtrate and washings were combined and concentrated in vacuo to give D-penicillamine hydrochloride. The hydrochloride was dissolved in ethanol, and the solution was filtered, adjusted to a pH of 5-6 with triethylamine with stirring and cooling, and allowed to stand. The crystals which formed were separated by filtration, washed with cold methanol, and dried in vacuo to give D-penicillamine as colorless crystals: yield 1.77 g (59.4%), m.p. 200°-202° C.

Workup

  1. filtrationthe solution was filtered
  2. temperaturecooling
  3. customThe crystals which formed
  4. customwere separated by filtration
  5. washwashed with cold methanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5ea715623ae14eac948087ca76d8a1c3
Source dataset
uspto-grants-1979_04
Patent number
US04150240

Linked notes

Loading…