Hydrochloric Acid → N-{4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethyl-phenyl}glycine

HRID 1007497Notes

Reaction equation

HRID 1007497 reaction equation
[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:19]([CH3:20])=[CH:18][C:17]([NH:21][CH2:22][C:23]([O:25]CC)=[O:24])=[CH:16][C:15]=3[CH3:28])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2].Cl>O1CCOCC1.[OH-].[Na+]>[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:19]([CH3:20])=[CH:18][C:17]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:16][C:15]=3[CH3:28])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22669446Ethyl N-{4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethylphenyl}glycinate

Product 1

HCID 9903147N-{4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethyl-phenyl}glycineYield 98.3%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

56 mg of ethyl N-{4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethylphenyl}glycinate (Example 3) are stirred in 7 ml of dioxane with 1.5 ml of IN sodium hydroxide for 2 hours at room temperature. The mixture is poured onto water, rendered acidic using 1N hydrochloric acid, extracted with ethyl acetate, the extract is dried and the solvent is removed in vacuo. 51 mg of N-{4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethyl-phenyl}glycine are obtained 1H-NMR (300 MHz, CDCl3): δ=1.29, d, 6H; 2.10, s, 6H; 3.07, sept., 1H; 3.70, s, 2H; 6.41, s, 2H; 6.73, m, 1H; 6.91, m, 2H; 7.21, d, 1H; 7.77, s, broad, 1H.

Workup

  1. additionThe mixture is poured onto water
  2. extractionextracted with ethyl acetate
  3. customthe extract is dried
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-5a03f96d9af9415d96bada032e48eb21
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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