Hydrochloric Acid → (4R)-3-(3-Bromopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid

HRID 647955

反応式

HRID 647955 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[NH:12][C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9]1.C(=O)([O-])[O-].[Na+].[Na+].[Br:22][CH2:23][CH2:24][C:25](Cl)=[O:26].Cl>O>[Br:22][CH2:23][CH2:24][C:25]([N:12]1[C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9][CH:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1])=[O:26]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 84944Propanoyl chloride, 3-bromo-HCID 2825745(4R)-2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid

生成物 1

HCID 54005883(4R)-3-(3-Bromopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid収率 70%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a stirred solution of 22.5 g of (4R)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid and 21.2 g of sodium carbonate in 200 ml of water, cooled by an ice-water bath, 18.8 g of 3-bromopropanoyl chloride is added dropwise. The resulting mixture is continuously stirred for 2 hr at room temperature, acidified with 2 N aqueous hydrochloric acid solution, and extracted with 300 ml of ethyl acetate. The organic layer is washed with brine and dried over sodium sulfate. After removal of ethyl acetate in vacuo, 100 ml of chloroform is added to the residue and the separated crystals are filtered to give 24.3 g (70%) of the product. The product is recrystallized from methanol to yield the titled compound: mp 109°-115° C.; IR (nujol) 3330, 1709, 1629, 1594, 1229, 1198, 1029 cm-1.

後処理

  1. extractionextracted with 300 ml of ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of ethyl acetate in vacuo, 100 ml of chloroform
  5. additionis added to the residue
  6. filtrationthe separated crystals are filtered

出典と根拠

ORDレコード
ord-3a4393fa201943759a4f43e54ebdd6bd
出典データセット
uspto-grants-1983_10
特許番号
US04410542

関連ノート

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