Hydrochloric Acid → (4-{2-[4-(1H-imidazol-1-yl)phenoxy]ethyl}-phenoxymethyl]benzoic acid

HRID 2112000ノート

反応式

HRID 2112000 の反応式
[N:1]1([C:6]2[CH:32]=[CH:31][C:9]([O:10][CH2:11][CH2:12][C:13]3[CH:30]=[CH:29][C:16]([O:17][CH2:18][C:19]4[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=4[C:21]([O:23]C)=[O:22])=[CH:15][CH:14]=3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[Li+].[OH-].Cl>C1COCC1.O>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][C:13]3[CH:30]=[CH:29][C:16]([O:17][CH2:18][C:19]4[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=4[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=3)=[CH:31][CH:32]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68869830methyl 2-[(4-{2-[4-(1H-imidazol-1-yl)phenoxy]ethyl}phenoxy)methyl]benzoate

生成物 1

HCID 9979166(4-{2-[4-(1H-imidazol-1-yl)phenoxy]ethyl}-phenoxymethyl]benzoic acid収率 4.7%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

Methyl 2-[(4-{2-[4-(1H-imidazol-1-yl)phenoxy]ethyl}phenoxy)methyl]benzoate (0.12 g, 0.28 mmol) was dissolved in a mixture of THF/water (7/1, 5 ml) and LiOH (0.03 g, 1.13 mmol) was added. The reaction was performed in a single node microwave oven (7 min, 150° C.). Workup by addition of HCl (1 ml, 1M), extract the product by adding two portions of EtOAc (5 ml). The pooled organic phases were dried (MgSO4) and the solvent was removed by evaporation. The crude was purified by preparative HPLC (starting with 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). Evaporation gave 6 mg of 2-[(4-{2-[4-(1H-imidazol-1-yl)phenoxy]ethyl}-phenoxymethyl]benzoic acid (yield 4.7%).

後処理

  1. additionwas added
  2. customThe reaction was performed in a single node microwave oven
  3. custom(7 min, 150° C.)
  4. extractionextract the product
  5. additionby adding two portions of EtOAc (5 ml)
  6. dry with materialThe pooled organic phases were dried (MgSO4)
  7. customthe solvent was removed by evaporation
  8. customThe crude was purified by preparative HPLC (
  9. concentrationthe acetonitrile concentration
  10. temperaturewas increased to 100%
  11. 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)
  12. additionThe product containing fractions
  13. customthe acetonitrile was removed by evaporation
  14. additionEtOAc (10 ml) was added
  15. washthe organic phase was washed with two portions of brine
  16. dry with materialdried (MgSO4)
  17. customEvaporation

出典と根拠

ORDレコード
ord-775d97d3d3dc418eafe8d937b8d6393a
出典データセット
uspto-grants-2009_04
特許番号
US07521461B2

反応ノート

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