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

HRID 1682767노트

반응식

HRID 1682767 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

500 ml of trifluoroacetic acid were added dropwise, whilst ice-cooling, 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 (e) above] in 700 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 4 hours. At the end of this time, the reaction mixture was freed from the methylene chloride solvent and the trifluoroacetic acid by distillation under reduced pressure, and a mixture of benzene and a small amount of ethyl acetate was added to the residue. The crystals which precipitated were collected by filtration and were recrystallized from a mixture of methanol and ethyl acetate, to give the title compound as crystals, melting at 162°166° C. [α]D23 -13.0° (c=0.885, methanol)

후처리

  1. distillationthe trifluoroacetic acid by distillation under reduced pressure
  2. additiona mixture of benzene
  3. additiona small amount of ethyl acetate was added to the residue
  4. customThe crystals which precipitated
  5. filtrationwere collected by filtration
  6. customwere recrystallized from a mixture of methanol and ethyl acetate

출처 및 근거

ORD 기록
ord-4dea9982f56040879f204bf76a0a8eb2
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05635534

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