Sodium hydride → 5-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-6-yloxy)-pentanoic acid ethyl ester

HRID 2292783Notes

Reaction equation

HRID 2292783 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:19][C:20]([NH2:22])=[O:21])=[C:7]([CH3:18])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][O:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:19][C:20]([NH2:22])=[O:21])=[C:7]([CH3:18])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1)[CH3:34]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerateHCID 105657326-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide

Product 1

HCID 106459145-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-6-yloxy)-pentanoic acid ethyl esterYield 710%

Procedure

Using the procedure in Example 33, 147 mg (0.5 mmol) of 6-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide was reacted with 20 mg (0.5 mmol) of 60% NaH/mineral oil and 0.08 mL (0.05 mmol) of ethyl 5-bromovalerate. After chromatography on silica (eluting first with 50% EtOAc/hexane, then EtOAc) and crystallization from MeOH/CH2Cl2 there was obtained 150 mg (71% yield) of 5-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-6-yl]oxy]pentanoic acid ethyl ester, mp, 123°-135° C.

Workup

  1. washAfter chromatography on silica (eluting first with 50% EtOAc/hexane
  2. customEtOAc) and crystallization from MeOH/CH2Cl2 there

Sources & evidence

ORD record
ord-fb1ae9cc4c9049109839a40129288daf
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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