Water → HCID 10737625, compound

HRID 1069633Notes

Reaction equation

HRID 1069633 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]([CH2:24][C:25]([NH2:27])=[O:26])=[C:9]([CH2:22][CH3:23])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].O.C(OCC)(=O)C>CO>[NH2:27][C:25](=[O:26])[CH2:24][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:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]=1[CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 10833640HCID 10833640, compound

Product 1

HCID 10737625HCID 10737625, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 100 mg (0.26 mmol) of 2-[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester and 2 mL of 1M NaOH in 6 mL of MeOH Tunas heated to dissolve all materials and then stirred at room temperature for 1 hour. Water and ethyl acetate were added and the aqueous layer separated, made acidic to pH 3 with 1N HCl and ethyl acetate added. The insoluble material was filtered. The ethyl acetate solution gas washed with brine, dried (MgSO4), and concentrated at reduced pressure. The residue was combined with the filtered material above to give 90 mg (95% yield) of 2-[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid, mp, 220-222° C.

Workup

  1. temperatureTunas heated
  2. dissolutionto dissolve all materials
  3. customthe aqueous layer separated
  4. additionadded
  5. filtrationThe insoluble material was filtered
  6. washThe ethyl acetate solution gas washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-d2b5f177805744a8bfd26dbdaf0f2a96
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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