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

HRID 898916

反応式

HRID 898916 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-59ac16dd3c83413d9b6be15b4d2dee24
出典データセット
uspto-grants-2008_04
特許番号
US07351858B2

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