Methanol → HCID 68485386, compound

HRID 1875032Notes

Reaction equation

HRID 1875032 reaction equation
[OH-].[Li+].[CH3:3][S:4]([NH:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:26]([O-:28])=[O:27])[N:14]2[C:17]([O:19]CCC(C)(C)C)=[O:18])=[CH:10][CH:9]=1)(=[O:6])=[O:5].CO.O>C1COCC1>[CH3:10][C:11]([O:19][C:17]([N:14]1[C:15]2[C:11](=[CH:10][CH:9]=[C:8]([NH:7][S:4]([CH3:3])(=[O:5])=[O:6])[CH:16]=2)[CH:12]=[C:13]1[C:26]([OH:28])=[O:27])=[O:18])([CH3:15])[CH3:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 86761650HCID 86761650, compound

Product 1

HCID 68485386HCID 68485386, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lithium hydroxide (0.068 g, 2.85 mmol) was added to a solution of 1-(1,1-dimethylethyl)2-ethyl 6-[(methylsulfonyl)amino]-1H-indole-1,2-dicarboxylate (0.109 g, 0.285 mmol) in THF:methanol:water/3:1:1 (3 mL). The mixture was heated at 50° C. for 2 hrs. The solvent was evaporated and the residue was dissolved in water, acidified with 1N aqueous HCl and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated to give the title compound (0.040 g, 55%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.92 (br. s., 1H), 11.41-11.79 (m, 1H), 9.32-9.73 (m, 1H), 7.48-7.57 (m, 1H), 7.31 (s, 1H), 6.94-7.00 (m, 1H), 6.88-6.94 (m, 1H), 2.88 (s, 3H). ES MS: m/z 253 (M−1).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0a79a36f301845d5848254ccf8f47133
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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