Sodium Hydroxide → HCID 86752077, compound

HRID 862359Notes

Reaction equation

HRID 862359 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[CH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH2:29][CH2:30][CH3:31])[CH:26]=2)[CH:21]([C:32]2[CH:37]=[CH:36][C:35]3[O:38][CH2:39][O:40][C:34]=3[CH:33]=2)[CH:20]1[C:41]([O-:43])=[O:42])([OH:3])=[O:2].[OH-].[Na+:45]>C(O)(C)C>[Na+:45].[Na+:45].[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[CH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH2:29][CH2:30][CH3:31])[CH:26]=2)[CH:21]([C:32]2[CH:37]=[CH:36][C:35]3[O:38][CH2:39][O:40][C:34]=3[CH:33]=2)[CH:20]1[C:41]([O-:43])=[O:42])([OH:3])=[O:2].[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[CH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH2:29][CH2:30][CH3:31])[CH:26]=2)[CH:21]([C:32]2[CH:37]=[CH:36][C:35]3[O:38][CH2:39][O:40][C:34]=3[CH:33]=2)[CH:20]1[C:41]([O-:43])=[O:42])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18427634HCID 18427634, compound

Product 1

HCID 86752077HCID 86752077, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of Methyl (1RS, 2SR, 3RS)-3-[2-[(4-Carboxypyridin-3-yl)oxy]-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (90, 0.15 mmol) in isopropanol (2 mL) was added 1M aqueous NaOH (0.3 mL, 0.3 mmol). The resulting mixture was heated to reflux for 12 h, then concentrated under reduced pressure. The residue was partitioned between dilute HCl and ethyl acetate. The ethyl acetate extract was washed with water and dried (Mg2SO4). The solvent was removed in vacuo. The residue was purified by flash column chromatography (silica gel, 30% ethyl acetate/hexanes containing 5% of acetic acid) to afford the title compound (65 mg, 74%); m.p. 220°-222° C. (dec.) (disodium salt).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 12 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between dilute HCl and ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. dry with materialdried (Mg2SO4)
  8. customThe solvent was removed in vacuo
  9. customThe residue was purified by flash column chromatography (silica gel, 30% ethyl acetate/hexanes containing 5% of acetic acid)

Sources & evidence

ORD record
ord-760c83bc5ce048e7a8315971e45f7ecd
Source dataset
uspto-grants-1998_02
Patent number
US05716984

Reaction notes

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