Ethyl Acetate → HCID 9863966, compound

HRID 650511Notes

Reaction equation

HRID 650511 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([C:23](=[O:27])[C:24]([NH2:26])=[O:25])=[C:9]([CH3:22])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].CCOC(C)=O>CO>[NH2:26][C:24](=[O:25])[C:23]([C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH2:4][C:3]([OH:28])=[O:2])[N:10]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:9]=1[CH3:22])=[O:27]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 10595929HCID 10595929, compound

Product 1

HCID 9863966HCID 9863966, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 660 mg (1.7 mmol) of ((3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetic acid methyl ester and 10 mL of 1N NaOH in 30 mL of methanol was heated to maintain reflux for 1 hour, cooled to room temperature and stirred for 0.5 hour. The mixture was concentrated at reduced pressure and the residue taken up in EtOAc/water. The aqueous layer was separated, made acidic to pH 2-3 with 1N HCl and extracted with EtOAc. On concentrating the EtOAc solution, 431 mg (69% yield) of ((3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetic acid crystallized, melting at 218-220° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 1 hour
  4. concentrationThe mixture was concentrated at reduced pressure
  5. customThe aqueous layer was separated
  6. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-8316504224a244bda614251038fc2a68
Source dataset
uspto-grants-2001_08
Patent number
US06274578B1

Reaction notes

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