Tetrahydrofuran → HCID 19603788, compound

HRID 1604664Notes

Reaction equation

HRID 1604664 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36]CC)=[O:35])=[CH:26][CH:27]=5)[C:22]([CH2:39][C:40]([O:42]C)=[O:41])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O1CCCC1>CO>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[CH:26][CH:27]=5)[C:22]([CH2:39][C:40]([OH:42])=[O:41])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 54489686HCID 54489686, compound

Product 1

HCID 19603788HCID 19603788, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-(4-ethoxycarbonylbutoxy)indole-3-acetate (0.2 g) and 1N-sodium hydroxide (1.66 ml) in a mixed solvent of tetrahydrofuran (2 ml) and methanol (1 ml) was stirred at room temperature for 4 hours. After removal of solvents, the aqueous solution was acidified with diluted hydrochloric acid. The resulting precipitates were collected by filtration and washed with water to give 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-(4-carboxybutoxy)indole-3-acetic acid (0.15 g).

Workup

  1. customAfter removal of solvents
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-043954dc9b8f4c20baa92b80ed9be437
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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