Methanol → HCID 23003911, compound

HRID 396710Notes

Reaction equation

HRID 396710 reaction equation
[C:1]1([CH3:37])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:36])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([N:19]2[C:27]3[C:22](=[CH:23][C:24]([CH:28]([CH3:35])[CH2:29][C:30]([O:32]CC)=[O:31])=[CH:25][CH:26]=3)[CH2:21][CH2:20]2)=[O:18])=[CH:12][CH:11]=1.[OH-].[Na+].CO>O1CCCC1>[C:1]1([CH3:37])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:36])[NH:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C:17]([N:19]2[C:27]3[C:22](=[CH:23][C:24]([CH:28]([CH3:35])[CH2:29][C:30]([OH:32])=[O:31])=[CH:25][CH:26]=3)[CH2:21][CH2:20]2)=[O:18])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 131724036HCID 131724036, compound

Product 1

HCID 23003911HCID 23003911, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl (R/S) 3-(1-{[4-(3-o-tolyl-ureido)-phenyl]-acetyl}-2,3-dihydro-1H-indol-5-yl)-butyrate [0.55 g, Reference Example 4(b)], aqueous sodium hydroxide solution (5.5 ml, 1M), methanol (5.5 ml) and tetrahydrofuran (11 ml) was stirred at room temperature overnight then evaporated to low bulk. The residue was diluted with water and the mixture was acidified by the addition of hydrochloric acid. The precipitate was collected by filtration, washed with water and then dried to give the title compound (0.41 g) as a white powder. LC-MS: RT=3.77 minutes (100% total area by ELS); MS (ES+) 472 (MH+), 494 (MNa+).

Workup

  1. customthen evaporated to low bulk
  2. additionThe residue was diluted with water
  3. additionthe mixture was acidified by the addition of hydrochloric acid
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-68ef38c9ec5f4d619f9145b37999bd41
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

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