Methanol → 6-(Tert-butoxycarbonylamino)-1h-indole-2-carboxylic acid

HRID 1874833Notes

Reaction equation

HRID 1874833 reaction equation
[OH-].[Li+].[CH3:3][C:4]([O:7][C:8]([NH:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[C:16]([C:20]([O:22]C)=[O:21])[NH:17]2)=[CH:13][CH:12]=1)=[O:9])([CH3:6])[CH3:5].C1COCC1.CO>O>[CH3:6][C:4]([O:7][C:8]([NH:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[C:16]([C:20]([OH:22])=[O:21])[NH:17]2)=[CH:13][CH:12]=1)=[O:9])([CH3:3])[CH3:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 23510173methyl 6-(tert-butoxycarbonylamino)-1H-indole-2-carboxylate

Product 1

HCID 594515396-(Tert-butoxycarbonylamino)-1h-indole-2-carboxylic acidYield 105.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium hydroxide (0.095 g, 3.96 mmol) was added to a solution of methyl 6-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate (0.115 g, 0.396 mmol) in a 3:1:1 mixture of THF:methanol:water (2 ml). The reaction mixture was stirred at RT overnight. The solvent was evaporated. The residue was dissolved in water and acidified with 1N aqueous HCl. The resulting suspension was extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate and the solvent was evaporated to give the title compound (0.115 g, >99%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.18 (s, 1H), 9.21 (s, 1H), 7.70 (s, 1H), 7.37 (d, 1H), 6.93 (dd, 1H), 6.74 (s, 1H), 1.46 (s, 9H). MS: m/z 275 (M−1).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in water
  3. extractionThe resulting suspension was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0307400d938d43dba031fc591c72b3db
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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