Penicillamine → 4-Thiazolidinecarboxylic acid, 2-(2-(dimethylamino)-2-oxoethyl)-2,5,5-trimethyl-

HRID 434548

反応式

HRID 434548 の反応式
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].[CH3:10][N:11]([CH3:18])[C:12](=[O:17])[CH2:13][C:14]([CH3:16])=O.S([O-])([O-])(=O)=O.[Mg+2]>C1C=CC=CC=1>[CH3:4][C:3]1([CH3:5])[S:6][C:14]([CH2:13][C:12]([N:11]([CH3:18])[CH3:10])=[O:17])([CH3:16])[NH:1][CH:2]1[C:7]([OH:9])=[O:8]

参加物

5

反応物 3

HCID 5852PenicillamineHCID 16278DimethylacetoacetamideHCID 24083Sulfuric acid magnesium salt (1:1)

生成物 1

HCID 30699314-Thiazolidinecarboxylic acid, 2-(2-(dimethylamino)-2-oxoethyl)-2,5,5-trimethyl-収率 66%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A suspension of 2.00 g (13.4 mmoles) of D-penicillamine and 1.73 g (13.4 mmoles) of N,N-dimethylacetoacetamide in 15 ml of dry benzene, and 0.6 g of anhydrous magnesium sulfate was refluxed for 3.5 hours under a stream of argon. The reaction mixture became clear and then the solvent was distilled off. The resulting residue was dissolved in hot methyl alcohol. Insolubles were removed by filtration and the solvent was again distilled off. The residue was crystallized from chloroform and further recrystallized from ethyl alcohol-ether to give 2.3 g of 4-carboxy-2,5,5-trimethylthiazolidine-2-N,N-dimethylacetamide as colorless prisms.

後処理

  1. temperaturewas refluxed for 3.5 hours under a stream of argon
  2. distillationthe solvent was distilled off
  3. dissolutionThe resulting residue was dissolved in hot methyl alcohol
  4. customInsolubles were removed by filtration
  5. distillationthe solvent was again distilled off
  6. customThe residue was crystallized from chloroform
  7. customfurther recrystallized from ethyl alcohol-ether

出典と根拠

ORDレコード
ord-dea7b4a90e8c42ab96f85ff15f067179
出典データセット
uspto-grants-1983_08
特許番号
US04398026

関連ノート

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