Tetrabutylammonium Fluoride → 5-(4-{2(R)-[2(R)-(3-Chlorophenyl)-2-hydroxyethyl-amino]propoxy}benzyl)thiazolidine-2,4-dione

HRID 1648447노트

반응식

HRID 1648447 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:21]=[C:22]([C@@H:26]([O:47][Si](C(C)(C)C)(C)C)[CH2:27][NH:28][C@H:29]([CH3:46])[CH2:30][O:31][C:32]2[CH:45]=[CH:44][C:35]([CH2:36][CH:37]3[S:41][C:40](=[O:42])[NH:39][C:38]3=[O:43])=[CH:34][CH:33]=2)[CH:23]=[CH:24][CH:25]=1>O1CCCC1>[Cl:19][C:20]1[CH:21]=[C:22]([C@@H:26]([OH:47])[CH2:27][NH:28][C@H:29]([CH3:46])[CH2:30][O:31][C:32]2[CH:45]=[CH:44][C:35]([CH2:36][CH:37]3[S:41][C:40](=[O:42])[NH:39][C:38]3=[O:43])=[CH:34][CH:33]=2)[CH:23]=[CH:24][CH:25]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 882931375-(4-{2(R)-[2(R)-(3-chlorophenyl)-2-t-butyldimethylsilyloxyethylamino]propoxy}benzyl)thiazolidine-2,4-dione

생성물 1

HCID 867488115-(4-{2(R)-[2(R)-(3-Chlorophenyl)-2-hydroxyethyl-amino]propoxy}benzyl)thiazolidine-2,4-dione

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

88 g of tetrabutylammonium fluoride were added to a solution of 46.2 g of 5-(4-{2(R)-[2(R)-(3-chlorophenyl)-2-t-butyldimethylsilyloxyethylamino]propoxy}benzyl)thiazolidine-2,4-dione [prepared as described in Preparation 3]in 500 ml of tetrahydrofuran, whilst ice-cooling, and the mixture was stirred at room temperature for 15 hours. At the end of this time, the tetrahydrofuran was distilled off under reduced pressure. The residue was then mixed with water and extracted with ethyl acetate. The extract was washed-with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, after which the solvent was distilled off under reduced pressure. The residue was then purified by column chromatography through silica gel, using a 5:1 by volume mixture of ethyl acetate and ethanol as the eluent, to obtain the title compound in the form of crude crystals. These crystals were then recrystallized from a mixture of ethyl acetate and ethanol to give 27.1 g of the title compound melting at between 100° C. and 112° C.

후처리

  1. customprepared
  2. temperaturecooling
  3. distillationAt the end of this time, the tetrahydrofuran was distilled off under reduced pressure
  4. additionThe residue was then mixed with water
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationafter which the solvent was distilled off under reduced pressure
  8. customThe residue was then purified by column chromatography through silica gel
  9. additionby volume mixture of ethyl acetate and ethanol as the eluent

출처 및 근거

ORD 기록
ord-f3f2c5f83bd44ce99e9b041396dfb9b4
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05436257

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