Trifluoroacetic acid → 5-{4-[2(R)-Aminopropoxy]benzyl}thiazolidine-2,4-dione trifluoroacetate

HRID 1648445ノート

反応式

HRID 1648445 の反応式
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([NH:15][C@H:16]([CH3:52])[CH2:17][O:18][C:19]1[CH:51]=[CH:50][C:22]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[N:26](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:25]2=[O:49])=[CH:21][CH:20]=1)=O)(C)(C)C>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:15][C@H:16]([CH3:52])[CH2:17][O:18][C:19]1[CH:51]=[CH:50][C:22]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:49])=[CH:21][CH:20]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 228549855-{4-[2(R)-t-butoxycarbonylaminopropoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione

生成物 1

HCID 228549835-{4-[2(R)-Aminopropoxy]benzyl}thiazolidine-2,4-dione trifluoroacetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

500 ml of trifluoroacetic acid were added dropwise to a solution of 85.5 g of 5-{4-[2(R)-t-butoxycarbonylaminopropoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione, [prepared as described in step (a), above] in 700 ml of methylene chloride, whilst ice-cooling, and the mixture was stirred at room temperature for 4 hours. At the end of this time, the reaction mixture was freed from methylene chloride and trifluoroacetic acid by distillation under reduced pressure. The residue was then triturated with a mixture of benzene and a small amount of ethyl acetate, and the crystals which precipitated were collected by filtration. These crystals were recrystallized from a mixture of methanol and ethyl acetate to give 36.9 g of the title compound melting at between 162° C. and 166° C.

後処理

  1. temperaturecooling
  2. distillationAt the end of this time, the reaction mixture was freed from methylene chloride and trifluoroacetic acid by distillation under reduced pressure
  3. customThe residue was then triturated with a mixture of benzene
  4. customa small amount of ethyl acetate, and the crystals which precipitated
  5. filtrationwere collected by filtration
  6. customThese crystals were recrystallized from a mixture of methanol and ethyl acetate

出典と根拠

ORDレコード
ord-a4868126da2d447fa02f5d34d8b71c39
出典データセット
uspto-grants-1995_07
特許番号
US05436257

反応ノート

読み込み中…