Sodium Hydroxide → HCID 58763423, compound

HRID 858286Notes

Reaction equation

HRID 858286 reaction equation
C([O:3][C:4]([C:6]1[N:7]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([O:29]C)=[O:28])[CH:22]=2)[C:8]2[C:13]([C:14]=1[CH2:15][C:16]([O:18]CC)=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+]>C1COCC1.CO.O>[C:16]([CH2:15][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([OH:29])=[O:28])[CH:22]=2)[C:6]=1[C:4]([OH:5])=[O:3])([OH:18])=[O:17]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58763428HCID 58763428, compound

Product 1

HCID 58763423HCID 58763423, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 3-ethoxycarbonylmethyl-1-(3-methoxycarbonyl-phenyl)-1H-indole-2-carboxylic acid ethyl ester (1.31 g, 3.2 mmol) in THF-methanol (2:1, 25 mL) was added a solution of NaOH (0.64 g, 16.0 mmol) in H2O (5 mL). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was diluted with H2O (50 mL) and washed with diethyl ether (50 mL). The aqueous layer was acidified with concentrated HCl to pH=1. The white precipitated was filtered off and dried in vacuo to afford 1.08 g of white solid (quantitative yield): 1H NMR (DMSO-d6) δ 4.13 (s, 2H), 7.05 (d, 1H), 7.21 (t, 1H), 7.31 (t, 1H), 7.62–7.71 (m, 2H), 7.76–7.82 (m, 2H), 8.01–8.05 (m, 1H); 13C NMR (DMSO-d6) 31.0, 111.1, 119.0, 121.2, 121.4, 126.2, 127.4, 127.8, 128.3, 128.7, 129.9, 132.2, 138.9, 139.3, 162.6, 167.0, 172.5. Anal: Calcd for C18H13NO6: C, 63.72; H, 3.86; N, 4.13. Found: C, 63.32; H, 4.08; N, 3.97.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with H2O (50 mL)
  3. washwashed with diethyl ether (50 mL)
  4. customThe white precipitated
  5. filtrationwas filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-cf7724e8476c4a6c8d6e63e157656c5f
Source dataset
uspto-grants-2006_12
Patent number
US07148250B2

Reaction notes

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