Ethyl Acetate → HCID 10544972, compound

HRID 1069639Notes

Reaction equation

HRID 1069639 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:22][C:23]([NH2:25])=[O:24])=[CH:9][N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].C(OCC)(=O)C>CO>[NH2:25][C:23](=[O:24])[CH2:22][C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH2:4][C:3]([OH:26])=[O:2])[N:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 10521936HCID 10521936, compound

Product 1

HCID 10544972HCID 10544972, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 100 mg (0.26 mmol) of 2-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester and 2 mL of 1N NaOH in 6 mL of MeOH was stirred at room temperature for 2 hours. Hater and ethyl acetate were added and the aqueous layer separated, made acidic to pH 3 with 1N HCl and ethyl acetate added. The ethyl acetate solution was washed with brine, dried (MgSO4), and concentrated at reduced pressure. The residue was stirred with methylene chloride and filtered to give 17 mg (56% yield) of 2-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid, mp, 207-208° C.

Workup

  1. customthe aqueous layer separated
  2. additionadded
  3. washThe ethyl acetate solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated at reduced pressure
  6. stirringThe residue was stirred with methylene chloride
  7. filtrationfiltered

Sources & evidence

ORD record
ord-fdd521a8359f47fa8339c7632c229c7c
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

Loading…