Acetic Acid → Penicillamine

HRID 26579

Reaction equation

HRID 26579 reaction equation
[CH3:1][C:2]1([CH3:24])[S:6]C(C(NC(CC2C=CC=CC=2)=O)C(O)=O)[NH:4][CH:3]1[C:21]([OH:23])=[O:22].COC1C=CC=C(N)C=1.C1(C)C=CC=CC=1.C(O)(=O)C>O>[NH2:4][C@@H:3]([C:21]([OH:23])=[O:22])[C:2]([SH:6])([CH3:24])[CH3:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 108243-MethoxyanilineHCID 98994Penicilloate

Product 1

HCID 5852Penicillamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.52 g (0.01 mole) of benzylpenicilloic acid, 3.70 g (0.03 mole) of m-anisidine and 20 ml of toluene were added to a solution of 3.60 g (0.06mole) of acetic acid in 30 ml of water. The mixture was heated under reflux, with stirring, for 4 hours in a nitrogen atmosphere. The reaction mixture was then treated as described in Example 9 to give D-penicillamine as colorless crystals: yield 1.07 g (71.8%), m.p. 201°-202° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. additionThe reaction mixture was then treated

Sources & evidence

ORD record
ord-1311a4fdba864b7e9c27194c25e7fbda
Source dataset
uspto-grants-1979_04
Patent number
US04150240

Linked notes

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