Sodium Hydroxide → HCID 18351695, compound

HRID 430799Notes

Reaction equation

HRID 430799 reaction equation
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[NH:8][CH2:9][CH2:10][N:11]2[C:19]3[C:14](=[C:15]([O:20][CH2:21][C:22]([O:24]C)=[O:23])[CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C.C1COCC1>[C:26]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:8][CH2:9][CH2:10][N:11]2[C:19]3[C:14](=[C:15]([O:20][CH2:21][C:22]([OH:24])=[O:23])[CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20708401HCID 20708401, compound

Product 1

HCID 18351695HCID 18351695, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl (1-(2-(N-(diphenylmethyl)amino)ethyl)indole-4-yloxy)acetate (99 mg) was dissolved in a mixed solvent of ethanol (5 ml) and THF (2 ml), and the obtained solution was stirred at room temperature. To this solution, 1N aqueous sodium hydroxide solution was added and the resulting solution was stirred at room temperature. After confirming vanishment of the materials, the solvent was removed under reduced pressure. Water (5 ml) was added to the obtained residue and 1N hydrochloric acid was added to the mixture to neutralize the same. The precipitated solids were collected by centrifugation and washed twice with water and twice with methanol. The solids were dried under reduced pressure to obtain the desired compound (58 mg, yield: 61%)

Workup

  1. stirringthe resulting solution was stirred at room temperature
  2. customthe solvent was removed under reduced pressure
  3. additionWater (5 ml) was added to the obtained residue and 1N hydrochloric acid
  4. additionwas added to the mixture
  5. customThe precipitated solids were collected by centrifugation
  6. washwashed twice with water and twice with methanol
  7. customThe solids were dried under reduced pressure

Sources & evidence

ORD record
ord-0f0b7891aba54da79d31dd090a5466cc
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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