HCID 10763855, compound → [[3-(2-amino-1,2-dioxoethyl)-2-cyclopropyl-1-(phenylmethyl)-1H-indol-4-yl]oxy)acetic acid

HRID 2256255Notes

Reaction equation

HRID 2256255 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([C:25](=[O:29])[C:26]([NH2:28])=[O:27])=[C:9]([CH:22]1[CH2:24][CH2:23]1)[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[OH-].[Na+].CO>[NH2:28][C:26](=[O:27])[C:25]([C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH2:4][C:3]([OH:30])=[O:2])[N:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]=1[CH:22]1[CH2:24][CH2:23]1)=[O:29]

Participants

4

Reactant 1

HCID 10763855HCID 10763855, compound

Product 1

HCID 9908515[[3-(2-amino-1,2-dioxoethyl)-2-cyclopropyl-1-(phenylmethyl)-1H-indol-4-yl]oxy)acetic acidYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 220 mg (0.54 mmol) of [[3-(2-amino-1,2-dioxoethyl)-2-cyclopropyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester in 5 mL of 1N NaOH and 15 mL of MeOH was heated to maintain reflux for 0.67 hours, concentrated at reduced pressure and the residue taken up in EtOAc/water. The aqueous layer was separated, made acidic with 1N HCl to pH 2-3 and EtOAc added. A precipitate formed and was separated to give 169 mg (80% yield) of [[3-(2-amino-1,2-dioxoethyl)-2-cyclopropyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid, mp, 246°-249° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 0.67 hours
  4. concentrationconcentrated at reduced pressure
  5. customThe aqueous layer was separated
  6. additionadded
  7. customA precipitate formed
  8. customwas separated

Sources & evidence

ORD record
ord-7d3be30f1bea44b29468a28b2d58416b
Source dataset
uspto-grants-1997_08
Patent number
US05654326

Reaction notes

Loading…