Lithium hydroxide, monohydrate → HCID 14882650, compound

HRID 330169Notes

Reaction equation

HRID 330169 reaction equation
O.[OH-].[Li+].[CH2:4]([N:7]1[C:15]2[C:10](=[CH:11][C:12](/[CH:16]=[C:17](/[C:19](=[O:24])[NH:20][CH2:21][CH2:22][CH3:23])\[CH3:18])=[CH:13][CH:14]=2)[C:9]([CH2:25][C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32]C)=[O:31])=[CH:28][C:27]=2[O:36][CH3:37])=[CH:8]1)[CH:5]=[CH2:6]>O.CO>[CH2:4]([N:7]1[C:15]2[C:10](=[CH:11][C:12](/[CH:16]=[C:17](/[C:19](=[O:24])[NH:20][CH2:21][CH2:22][CH3:23])\[CH3:18])=[CH:13][CH:14]=2)[C:9]([CH2:25][C:26]2[CH:35]=[CH:34][C:29]([C:30]([OH:32])=[O:31])=[CH:28][C:27]=2[O:36][CH3:37])=[CH:8]1)[CH:5]=[CH2:6]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86743691HCID 86743691, compound

Product 1

HCID 14882650HCID 14882650, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of lithium hydroxide monohydrate (0.16 g) in water (2 ml) was added to a stirred solution of methyl E-4[1-allyl-5-[2-(propylcarbamoyl)- 1-propenyl]indol-3-ylmethyl]-3-methoxybenzoate (0.34 g) in methanol (5 ml), and the mixture was stirred for 18 hr under an atmosphere of nitrogen. The solution was concentrated to remove methanol, acidified with 1M hydrochloric acid (30 ml), diluted with water (30 ml), and the precipitate which formed (0.31 g) was isolated by filtration and dried. The product was dissolved in methanol (2 ml) and water (2 ml), and triethylamine (0.1 ml) was added. The salt that formed was purified by reverse-phase flash chromatography on octadecylsilyl (ODS, J. T. Baker) 40 micron packing material (40 g), eluting with 1:1 methanol:water. The fraction containing the purified salt was evaporated and acidified with 1M hydrochloric acid, extracted with methylene chloride (3×50 ml), and the organic phase washed with 1M hydrochloric acid and brine, and dried (MgSO4). The solvent was evaporated to give the title compound (0.29 g, 88%) as a solid glass, mp 84°-90°.

Workup

  1. concentrationThe solution was concentrated
  2. customto remove methanol
  3. additiondiluted with water (30 ml)
  4. customthe precipitate which formed (0.31 g)
  5. customwas isolated by filtration
  6. customdried
  7. dissolutionThe product was dissolved in methanol (2 ml)
  8. additionwater (2 ml), and triethylamine (0.1 ml) was added
  9. customThe salt that formed
  10. customwas purified by reverse-phase flash chromatography on octadecylsilyl (ODS, J. T. Baker) 40 micron
  11. washeluting with 1:1 methanol
  12. additionThe fraction containing the purified salt
  13. customwas evaporated
  14. extractionextracted with methylene chloride (3×50 ml)
  15. washthe organic phase washed with 1M hydrochloric acid and brine
  16. dry with materialdried (MgSO4)
  17. customThe solvent was evaporated

Sources & evidence

ORD record
ord-77c2029c66314b998328e9a52054a0a9
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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