Hydrochloric Acid → HCID 9893655, compound

HRID 396711Notes

Reaction equation

HRID 396711 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:23]2[C:31]3[C:26](=[CH:27][C:28]([CH:32]([CH2:38][C:39]([O:41]C)=[O:40])[CH2:33][C:34]([O:36]C)=[O:35])=[CH:29][CH:30]=3)[CH2:25][CH2:24]2)=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].[OH-].[Na+].Cl>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:23]2[C:31]3[C:26](=[CH:27][C:28]([CH:32]([CH2:33][C:34]([OH:36])=[O:35])[CH2:38][C:39]([OH:41])=[O:40])=[CH:29][CH:30]=3)[CH2:25][CH2:24]2)=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23004007HCID 23004007, compound

Product 1

HCID 9893655HCID 9893655, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A stirred suspension of dimethyl 3-(1-{[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-2,3-dihydro-1H-indol-5-yl)-pentanedioate [270 mg, Reference Example 4(c)] in ethanol (10 ml) was treated with a solution of sodium hydroxide (190 mg) in water (2 ml) and the mixture stirred at reflux for 3 hours. After cooling to room temperature the mixture was treated with water (10 ml) and then carefully acidified to pH1 by the addition of hydrochloric acid (3M) with ice cooling. the resultant precipitate was collected by filtration, then dried and then recrystallised from ethyl acetate to give the title compound (60 mg) as a white crystalline solid. LC-MS: RT=2.44 minutes (100% total area by ELS); MS (ES+) 568 (MNa+).

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationthe resultant precipitate was collected by filtration
  3. customdried
  4. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-ddd03a2b0949413590b0a7a54ea25534
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

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