Potassium Hydroxide → (R)-[3-(2-(tert-butoxycarbonylamino)propyl)-1H-indol-7-yloxy]acetic acid

HRID 1351928Notes

Reaction equation

HRID 1351928 reaction equation
C(N(CC)[C:4]([CH2:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[C:13]2[CH2:17][C@H:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19])=[O:5])C.[OH-:30].[K+]>O.C(O)C>[C:23]([O:22][C:21]([NH:20][C@H:18]([CH3:19])[CH2:17][C:13]1[C:12]2[C:16](=[C:8]([O:7][CH2:6][C:4]([OH:30])=[O:5])[CH:9]=[CH:10][CH:11]=2)[NH:15][CH:14]=1)=[O:27])([CH3:24])([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12045561tert-butyl (R)-[2-(7-diethylcarbamoylmethoxy-1H-indol-3-yl)-1-methylethyl]carbamate

Product 1

HCID 69459193(R)-[3-(2-(tert-butoxycarbonylamino)propyl)-1H-indol-7-yloxy]acetic acidYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl (R)-[2-(7-diethylcarbamoylmethoxy-1H-indol-3-yl)-1-methylethyl]carbamate (0.35 g, 0.87 mmol) and potassium hydroxide (0.39 g, 7 mmol) in water (4 mL) and ethanol (6 mL) is stirred at 60° C. for 8 hours. After cooling, the mixture is concentrated and acidified by addition of water (30 mL) and acetic acid. The resultant is extracted with chloroform, washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to give the desired (R)-[3-(2-(tert-butoxycarbonylamino)propyl)-1H-indol-7-yloxy]acetic acid (0.30 g, yield: 100%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated
  3. additionacidified by addition of water (30 mL) and acetic acid
  4. extractionThe resultant is extracted with chloroform
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6cd857436958414c8acd47d0f48d9969
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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