HCID 86601924, compound → HCID 10456025, compound

HRID 2112004Notes

Reaction equation

HRID 2112004 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:32]=[CH:31][C:9]([O:10][CH2:11][CH2:12][C:13]2[CH:30]=[CH:29][C:16]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=3[C:21]([O:23]C)=[O:22])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3]>O1CCCC1.O.Cl>[CH3:1][S:2]([O:5][C:6]1[CH:32]=[CH:31][C:9]([O:10][CH2:11][CH2:12][C:13]2[CH:30]=[CH:29][C:16]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=3[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

5

Reactant 1

HCID 86601924HCID 86601924, compound

Product 1

HCID 10456025HCID 10456025, compoundYield 7.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-{[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenoxy]methyl}benzoate (0.18 g, 0.38 mmol) was dissolved in a mixture of tetrahydrofuran and water 7:1 (5 ml). The reaction was performed in a single node microwave oven (150° C. in 7 minutes). The mixture was diluted with HCl (2 ml, 1 M) and the organic phase was isolated. 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 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). Removing the solvent by evaporation gave 13 mg of 2-{[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenoxy]-methyl}benzoic acid (yield 7.7%).

Workup

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

Sources & evidence

ORD record
ord-7c06963712a746a0b8d0c1dc3b642f40
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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