Sodium hydride → HCID 86751502, compound

HRID 2292792Notes

Reaction equation

HRID 2292792 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]1[CH2:23][CH2:22][CH2:21][CH:20](CC(N)=O)[CH2:19]1)[C:13]([CH3:28])=[CH:12]2)[CH3:2].C1(N2C3C(=CC(O)=CC=3)C([CH2:46][C:47]([NH2:49])=[O:48])=C2C)CCCCC1.[H-].[Na+].BrCCCC(OCC)=O>>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:13]([CH3:28])=[C:12]2[CH2:46][C:47]([NH2:49])=[O:48])[CH3:2]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 21191869HCID 21191869, compoundHCID 86751503HCID 86751503, compound

Product 1

HCID 86751502HCID 86751502, compoundYield 46%

Procedure

[4-[[3-(2-Amino-2-oxoethyl)-cyclohexyl-2-methyl-1-H-indol-5-yl]oxy]butanoic acid ethyl ester. 1-Cyclohexyl-5-hydroxy-2-methyl-1H-indole-3-acetamide (300 mg, 1.0 mmol) was reacted with 40 mg (1.0 mmol) of 60% NaH/mineral oil and then 0.143 mL (1.0 mmol) of ethyl 4-bromobutyrate as described in Example 50, Part D to give a product that was chromatographed on silica gel (eluted with 2% MeOH/methylene chloride) to give 190 mg (46% yield) of [4-[[3-(2-amino-2-oxoethyl)-1-cyclohexyl-2-methyl-1-H-indol-5-yl]oxy]butanoic acid ethyl ester, mp, 92°-94° C.

Workup

  1. customto give a product that
  2. customwas chromatographed on silica gel (eluted with 2% MeOH/methylene chloride)

Sources & evidence

ORD record
ord-ec0ef9b0a76b4575a2797a6115e0b186
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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