Sodium hydride → HCID 11795730, compound

HRID 2292785Notes

Reaction equation

HRID 2292785 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:19][C:20]([NH2:22])=[O:21])=[C:5]([CH3:18])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Br[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>O>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:19][C:20]([NH2:22])=[O:21])=[C:5]([CH3:18])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:33]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 10541824HCID 10541824, compound

Product 1

HCID 11795730HCID 11795730, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 294 mg (1 mmol) of 4-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide was treated with 40 mg mmol) of 60% NaH/mineral oil and after 1 hour, 0.15 mL (1 mmol) of ethyl 4-bromobutyrate was added. The mixture was stirred for 2 hours, diluted with water and extracted with EtOAc. The EtOAc solution was washed with NaCl solution, dried (MgSO4), and concentrated at reduced pressure. The residue was crystallized from MeOH/hexane to give a total of 235 mg (58% yield) of 4-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]butanoic acid ethyl ester, mp, 115°-116° C.

Workup

  1. extractionextracted with EtOAc
  2. washThe EtOAc solution was washed with NaCl solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was crystallized from MeOH/hexane

Sources & evidence

ORD record
ord-1013482e8fa24c46a386b901a3c74e08
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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