Penicillamine → HCID 15725082, compound

HRID 867415Notes

Reaction equation

HRID 867415 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:11])[C:9]=1[OH:10])[CH:5]=O.[NH2:12][C@@H:13]([C:18]([OH:20])=[O:19])[C:14]([SH:17])([CH3:16])[CH3:15]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[NH:12][C@@H:13]([C:18]([OH:20])=[O:19])[C:14]([CH3:16])([CH3:15])[S:17]2)[CH:7]=[C:8]([Br:11])[C:9]=1[OH:10]

Participants

4

Reactant 2

HCID 5852PenicillamineHCID 181003,5-Dibromo-4-Hydroxybenzaldehyde

Product 1

HCID 15725082HCID 15725082, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution containing 5.6 g (20 mmoles) of 3,5-dibromo-4-hydroxybenzaldehyde and 3 g (20 mmoles) of D-penicillamine in 100 ml of 30% methanol is stirred for 16 hours. The precipitated product is filtered and washed with aqueous methanol to give 6.77 g (82.3%) of the title acid which can be recrystallized from a mixture containing ethanol, dimethylformamide and water, m.p.: 154°-155° C., [α]D25 =+87° (c=1.362, dimethylsulphoxide).

Workup

  1. filtrationThe precipitated product is filtered
  2. washwashed with aqueous methanol

Sources & evidence

ORD record
ord-51966de0033743198b1e2a5528996893
Source dataset
uspto-grants-1988_10
Patent number
US04775675

Reaction notes

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