Trifluoroacetic acid → [4-(2-{[2-(Methoxycarbonyl)phenyl]thio}ethyl)phenoxy]acetic acid

HRID 898916

반응식

HRID 898916 반응식
C([O:5][C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17][C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[C:20]([O:22][CH3:23])=[O:21])=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:23][O:22][C:20]([C:19]1[CH:24]=[CH:25][CH:26]=[CH:27][C:18]=1[S:17][CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]([OH:28])=[O:5])=[CH:14][CH:13]=1)=[O:21]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 69259277Methyl 2-({2-[4-(2-tert-butoxy-2-oxoethoxy)phenyl]ethyl}thio)benzoate

생성물 1

HCID 57640312[4-(2-{[2-(Methoxycarbonyl)phenyl]thio}ethyl)phenoxy]acetic acid수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Methyl 2-({2-[4-(2-tert-butoxy-2-oxoethoxy)phenyl]ethyl}thio)benzoate (4.630 g, 11.502 mmol) was take up in DCM (50 ml) and treated with trifluoroacetic acid (44.40 g, 389.405 mmol) at r.t for 4 h. The mixture was evaporated and azeotroped with toluene. The crude was purified by preparative HPLC (started with isocratic acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min). The product containing fractions were pooled and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4). The solvent was removed by evaporation to give 3.825 g of [4-(2-{[2-(methoxycarbonyl)phenyl]thio}ethyl)-phenoxy]acetic acid (yield for two steps 63.9% overall).

후처리

  1. customThe mixture was evaporated
  2. customazeotroped with toluene
  3. customThe crude was purified by preparative HPLC (
  4. concentrationthe acetonitrile concentration
  5. temperaturewas increased to 100%
  6. additiona mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min)
  7. additionThe product containing fractions
  8. customthe acetonitrile was removed by evaporation
  9. additionEtOAc (10 ml) was added
  10. washthe organic phase was washed with two portions of brine
  11. dry with materialdried (MgSO4)
  12. customThe solvent was removed by evaporation

출처 및 근거

ORD 기록
ord-59ac16dd3c83413d9b6be15b4d2dee24
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07351858B2

연결된 노트

불러오는 중…