Hydrochloric Acid → HCID 10712971, compound

HRID 2292770Notes

Reaction equation

HRID 2292770 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]([CH3:23])=[C:10]2[CH2:24][C:25]([NH2:27])=[O:26])C.[OH-].[Na+].Cl>CCO.C1COCC1>[NH2:27][C:25](=[O:26])[CH2:24][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([O:6][CH2:5][C:4]([OH:28])=[O:3])[CH:8]=2)[N:12]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:11]=1[CH3:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10643497HCID 10643497, compound

Product 1

HCID 10712971HCID 10712971, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 190 mg (0.5 mmol) of 2-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]acetic acid ethyl ester and 2 mL of 5N NaOH in 30 mL of EtOH and 10 mL of THF was stirred for approximately 15 hours, the mixture made acidic with 5N HCl and extracted with EtOAc. The EtOAc solution was washed with saturated NaCl solution, dried (Na2SO4), and concentrated at reduced pressure. The residue was washed with ether to give 155 mg (90% yield) of 2-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]acetic acid, mp, 196°-198° C.

Workup

  1. extractionextracted with EtOAc
  2. washThe EtOAc solution was washed with saturated NaCl solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated at reduced pressure
  5. washThe residue was washed with ether

Sources & evidence

ORD record
ord-16e417b5329c444f823dd1e388df4e74
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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