Triethylamine → (4R)-3-[3-(2-Carboxyethyldisulfanyl)propanoyl]-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid

HRID 647956

반응식

HRID 647956 반응식
[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(N(CC)CC)C.[C:23]1(=[O:33])[O:32][C:30](=[O:31])[CH2:29][CH2:28][S:27][S:26][CH2:25][CH2:24]1>CC(C)=O>[C:23]([CH2:24][CH2:25][S:26][S:27][CH2:28][CH2:29][C:30]([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:31])([OH:33])=[O:32]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 2825745(4R)-2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acidHCID 542945991,5,6-Oxadithionane-2,9-dione

생성물 1

HCID 13053751(4R)-3-[3-(2-Carboxyethyldisulfanyl)propanoyl]-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a stirred solution of 2.0 g of (4R)-2-hydroxyphenyl-4-thiazolidinecarboxylic acid and 1.7 ml of triethylamine in 15 ml of anhydrous acetone, 2.0 g of dithiodipropanoic anhydride is added. The resulting mixture is continuously stirred for 40 min at room temperature and extracted with ethyl acetate after addition of 50 ml of water containing a small amount of potassium carbonate. The aqueous layer is acidified with N aqueous hydrochloric acid and extracted with ethyl acetate. The second organic layer is washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residual oil is purified by column chromatography on silica gel to give crystals of the titled compound. The yield is 0.6 g (15%).

후처리

  1. extractionextracted with ethyl acetate
  2. additionafter addition of 50 ml of water containing a small amount of potassium carbonate
  3. extractionextracted with ethyl acetate
  4. washThe second organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residual oil is purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-0be0cd70bff4422d92c316d2e1d9d1de
출처 데이터셋
uspto-grants-1983_10
특허 번호
US04410542

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