Hydrochloric Acid → 2-({4-[3-(4-Hydroxyphenoxy)propyl]phenoxy}methyl)benzoic acid

HRID 2112028노트

반응식

HRID 2112028 반응식
CS([O:5][C:6]1[CH:33]=[CH:32][C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:31]=[CH:30][C:17]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=3[C:22]([O:24]C)=[O:23])=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)(=O)=O.[OH-].[Li+].Cl>C1COCC1.O>[OH:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:31]=[CH:30][C:17]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=3[C:22]([OH:24])=[O:23])=[CH:16][CH:15]=2)=[CH:32][CH:33]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86601926Methyl 2-{[4-(3-{4-[(methylsulfonyl)oxy]phenoxy}propyl)phenoxy]methyl}benzoate

생성물 1

HCID 104522502-({4-[3-(4-Hydroxyphenoxy)propyl]phenoxy}methyl)benzoic acid수율 20.6%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

Methyl 2-{[4-(3-{4-[(methylsulfonyl)oxy]phenoxy}propyl)phenoxy]methyl}benzoate (0.38 g, 0.81 mmol) was dissolved in a mixture of THF/water (7/1, 4 ml) and lithium hydroxide (9.3 mg, 0.39 mmol) was added. The reaction was performed in a single node microwave oven (7 min, 150° C.). The reaction mixture was acidified (HCl, 1 M, 1 ml) and the water phase was washed with two portions of EtOAc (2×5 ml). The organic phases were combined, dried (MgSO4) and the solvent was removed by evaporation the crude was purified by preparative HPLC (started 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 was 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). Removing the solvent by evaporation gave 63 mg of 2-({4-[3-(4-hydroxyphenoxy)propyl]phenoxy}methyl)benzoic acid (yield 20.5%).

후처리

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

출처 및 근거

ORD 기록
ord-2d3509ed49ff4e59a9249131b7178384
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521461B2

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