Penicillamine → 75323-55-6

HRID 1460410Notes

Reaction equation

HRID 1460410 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].[OH-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O=O>[CH2:12]([S:6][C:3]([CH3:5])([CH3:4])[C@H:2]([C:7]([OH:9])=[O:8])[NH2:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 5852PenicillamineHCID 7498Benzyl BromideHCID 14798Sodium Hydroxide2×

Product 1

HCID 50404575323-55-6Yield 70.1%

Reagents, catalysts & solvents 1

HCID 977OxygenSolvent2×

Procedure

D-Penicillamine (5)(140 9: 938 mmol) and sodium hydroxide (43 g; 938 mmol) were dissolved in a mixture of oxygen-free water (670 ml) and oxygen-free isopropanol (830 ml) at 0° C. To the resultant solution, benzyl bromide (208.6 g; 1219 mmol) was dropwise added, and the mixture was stirred at room temperature overnight. The reaction mixture was made neutral with 2N aqueous sodium hydroxide, stirred at -20° C. to precipitate crystals, which were collected by filtration to give Compound (6) (157.3 g; yield 70%).

Workup

  1. stirringstirred at -20° C.
  2. customto precipitate crystals, which
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-6bf9a2abf7af4d3ca2526a2f1604197f
Source dataset
uspto-grants-1991_12
Patent number
US05071636

Reaction notes

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