Methanol → HCID 57901795, compound

HRID 1874820Notes

Reaction equation

HRID 1874820 reaction equation
[OH-].[Li+].[CH3:3][C:4]([O:7][C:8]([NH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][C:17]([C:20]([O:22]CC)=[O:21])=[CH:16]2)=[O:9])([CH3:6])[CH3:5].CO.O>C1COCC1>[CH3:6][C:4]([O:7][C:8]([NH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16]2)=[O:9])([CH3:3])[CH3:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 57901606HCID 57901606, compound

Product 1

HCID 57901795HCID 57901795, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.196 g, 8.18 mmol) was added to a solution of ethyl 7-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate (0.249 g, 0.818 mmol) in THF:MeOH:water/3:1:1 (5 mL). The mixture was stirred at RT overnight. The solvent was evaporated and the residue was dissolved in water, acidified with 6N aqueous HCl, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to give the title compound (0.206 g, 90%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 11.36 (s, 1H), 9.29 (s, 1H), 7.28-7.53 (m, 2H), 7.14-7.28 (m, 2H), 6.97-7.13 (m, 1H), 1.41-1.80 (m, 9H). MS m/z 277 (M+1).

Workup

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

Sources & evidence

ORD record
ord-baa5c9b10c744eae9f3906e0a0b2d336
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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