Sodium Hydroxide → 4-[(2,3-Dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl-acetic acid

HRID 1167810Notes

Reaction equation

HRID 1167810 reaction equation
[N:1]1([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]C)=[O:21])=[CH:15][C:14]=2[O:24][CH3:25])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[N:1]1([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][C:14]=2[O:24][CH3:25])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54400434Methyl 4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl-acetate

Product 1

HCID 229942374-[(2,3-Dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl-acetic acidYield 86.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl-acetate (5.2 g, Reference Example 6) and sodium hydroxide (20 mL, 1M) in methanol (100 mL) and water (50 mL) was stirred at 50° C. for 4 hours. The mixture was evaporated to low bulk and the aqueous layer was washed with dichloromethane then acidified with hydrochloric acid (1M) to give a tan precipitate. This material was filtered, washed with water, then with ether and then dried to give the title compound (4.3 g) as an off-white solid. HPLC: RT=13.3 minutes (99% by ELS).

Workup

  1. customThe mixture was evaporated to low bulk
  2. washthe aqueous layer was washed with dichloromethane
  3. customto give a tan precipitate
  4. filtrationThis material was filtered
  5. washwashed with water
  6. dry with materialwith ether and then dried

Sources & evidence

ORD record
ord-3265323037e549218ea3085dcf0b2b60
Source dataset
uspto-grants-2003_09
Patent number
US06620832B2

Reaction notes

Loading…