Sodium hydride → HCID 57586486, compound

HRID 420402Notes

Reaction equation

HRID 420402 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2].[C:30]([O:34][C:35]([NH:37][C:38]1[CH:43]=[C:42]([I:44])[CH:41]=[C:40]([I:45])[CH:39]=1)=[O:36])([CH3:33])([CH3:32])[CH3:31].[H-].[Na+]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:37]([C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:36])[C:38]2[CH:39]=[C:40]([I:45])[CH:41]=[C:42]([I:44])[CH:43]=2)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 21575514HCID 21575514, compoundHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Product 1

HCID 57586486HCID 57586486, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (3.6 g, 7.6 mmol), N-tert-butoxycarbonyl-3,5-diiodoaniline (2.8 g, 6.3 mmol) in DMF (60 mL) was added NaH (60% dispersion in mineral oil), (504 mg, 12.6 mmol). The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with EtOAc (120 mL), then washed with brine. The organic phase was dried over Na2SO4 and evaporated under reduced pressure. Purification by Isco chromatography (Gradient of 20 minutes from hexanes to Hexanes/EtOAc 80%) afforded the title compound (3.3 g, 60%) as a light yellow oil. HR-ES(+): calculated for C34H47N1O7I2 (M+Na)+ 858.1334, found 858.1325.

Workup

  1. washwashed with brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated under reduced pressure
  4. customPurification by Isco chromatography (Gradient of 20 minutes from hexanes to Hexanes/EtOAc 80%)

Sources & evidence

ORD record
ord-8207e37f095f48a3b5c40c7a54f684d9
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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