Methanol → HCID 59451365, compound

HRID 1874811Notes

Reaction equation

HRID 1874811 reaction equation
[CH3:1][C:2]1([CH3:31])[O:6][C@@H:5]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([C:19]([O:21]CCC(C)(C)C)=[O:20])[C:14]([C:28]([O-:30])=[O:29])=[CH:13]3)[CH2:4][O:3]1.[Li+].[OH-].[CH2:34]1[CH2:38]OC[CH2:35]1.[CH3:39]O>>[CH3:31][C:2]1([CH3:1])[O:6][C@@H:5]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([C:19]([O:21][C:34]([CH3:35])([CH3:38])[CH3:39])=[O:20])[C:14]([C:28]([OH:30])=[O:29])=[CH:13]3)[CH2:4][O:3]1

Participants

5

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86761644HCID 86761644, compound

Product 1

HCID 59451365HCID 59451365, compound

Procedure

To a solution of 1-(1,1-dimethylethyl)2-ethyl 5-({2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl}oxy)-1H-indole-1,2-dicarboxylate (167 mg, 0.385 mmol) in MeOH (2 mL) was added 1N LiOH (0.58 mL). A precipitate appeared and THF (2 mL) was added. The solution was stirred until TLC showed the starting material had been consumed. The reaction mixture was quenched with 1N HCl (0.58 mL) and the solvent evaporated. The residue was dissolved in EtOAc and extracted with 1N NaOH. The aqueous layer was acidified with conc. HCl until a precipitate formed and then partitioned with EtOAc. The organic layer was separated, dried over MgSO4 and the solvent evaporated. The crude material was directly with no further purification.

Workup

  1. customhad been consumed
  2. customThe reaction mixture was quenched with 1N HCl (0.58 mL)
  3. customthe solvent evaporated
  4. dissolutionThe residue was dissolved in EtOAc
  5. extractionextracted with 1N NaOH
  6. customformed
  7. custompartitioned with EtOAc
  8. customThe organic layer was separated
  9. dry with materialdried over MgSO4
  10. customthe solvent evaporated
  11. customThe crude material was directly with no further purification

Sources & evidence

ORD record
ord-1d30dfccf0764516a2fb5b7b8c682f7a
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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