Water → HCID 67036172, compound

HRID 1623433Notes

Reaction equation

HRID 1623433 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C:6]1=[O:22].O.[OH-].[Li+]>C1(C)CCC(C(C)C)C(O)C1>[O:22]=[C:6]1[C:7](=[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:15])[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]1[CH2:4][C:3]([OH:23])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67036305HCID 67036305, compound

Product 1

HCID 67036172HCID 67036172, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 1254MentholSolvent

Procedure

[2-Oxo-3-(1-phenyl-ethylidene)-2,3-dihydro-indol-1-yl]-acetic acid methyl ester (50 mg, 0.16 mmol) was dissolved in menthol 1 ml; then 0.1 ml water was added. Finally, lithium hydroxide (10 mg) was added. The mixture was stirred overnight. The reaction was monitored by HPLC. When the reaction was finished, the solvent was removed under reduced pressure. The residue was dissolved in 2 ml DMF for prepared HPLC to give [2-oxo-3-(1-phenyl-ethylidene)-2,3-dihydro-indol-1-yl]-acetic acid as white powder (11 mg). 1H NMR (400 MHz, CDCl3) δ ppm 2.82 (s, 3H) 4.61 (s, 2H) 6.20 (d, J=7.58 Hz, 1H) 6.66-6.73 (m, 2H) 7.14 (t, J=7.58 Hz, 1H) 7.31 (s, 2H) 7.46-7.54 (m, 3H). MS calcd. for C18H15NO3 293, obsd. (ESI+) [(M+H)+]294.1.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 2 ml DMF
  3. customfor prepared HPLC

Sources & evidence

ORD record
ord-cfad4211dbf7484384202e50c5b8bee2
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

Loading…