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

HRID 2112000

반응식

HRID 2112000 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-775d97d3d3dc418eafe8d937b8d6393a
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521461B2

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