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Potassium Carbonate → 4-Carboxy-N-(2,2-dimethyl-3-nitroxypropionyl)-2-phenylthiazolidine

HRID 1770213
ノート
印刷プレビュー

反応式

HRID 1770213 の反応式
[CH3:1][C:2]([CH3:11])([CH2:6][O:7][N+:8]([O-:10])=[O:9])[C:3](Cl)=[O:4].[C:12]([CH:15]1[CH2:19][S:18][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:16]1)([OH:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[C:12]([CH:15]1[CH2:19][S:18][CH:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:16]1[C:3](=[O:4])[C:2]([CH3:11])([CH3:1])[CH2:6][O:7][N+:8]([O-:10])=[O:9])([OH:14])=[O:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 392372-Phenylthiazolidine-4-carboxylic acidHCID 200955153-Chloro-2,2-dimethyl-3-oxopropyl nitrate

生成物 1

HCID 677785314-Carboxy-N-(2,2-dimethyl-3-nitroxypropionyl)-2-phenylthiazolidine収率 38%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

A solution of 5.2 g of 2,2-dimethyl-3-nitroxypropanoyl chloride in 100 ml of tetrahydrofuran was added at 0° C. under nitrogen to a solution of 6.0 g of 4-carboxy-2-phenylthiazolidine and 4.0 g of potassium carbonate in a mixture of 50 ml of tetrahydrofuran and 150 ml of water. After stirring the resulting solution for 45 minutes the mixture was concentrated under reduced pressure to about 150 ml and then acidified to pH=2 with citric acid. The resulting mixture was extracted with diethyl ether and the organic phase was dried over sodium sulphate and evaporated. The residue was purified by chromatography (silica, petroleum ether 60-80: ethyl acetate: acetic acid/8:8:1). Yield 38%. Empirical formula C15H18N2O6S. Molecular weight 354. Melting point 35°-38° C. TLC system: petroleum ether 60-80: ethyl acetate: acetic acid/4:4:1. Rf 0.50.

後処理

  1. concentrationwas concentrated under reduced pressure to about 150 ml
  2. extractionThe resulting mixture was extracted with diethyl ether
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by chromatography (silica, petroleum ether 60-80: ethyl acetate: acetic acid/8:8:1)

出典と根拠

ORDレコード
ord-707e8f9929274e4d80a83760980aa464
出典データセット
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05385922

反応ノート

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