Sodium hydride → HCID 54222911, compound

HRID 2119844Notes

Reaction equation

HRID 2119844 reaction equation
[H-].[Na+].[OH:3][C@@H:4]([CH2:20][N:21]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:5][O:6][C:7]1[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.Br[C:34]([CH3:39])([CH3:38])[C:35]([NH2:37])=[O:36]>O1CCOCC1>[OH:3][C@@H:4]([CH2:20][N:21]([C:26]1[CH:31]=[CH:30][C:29]([O:32][C:34]([CH3:39])([C:35](=[O:36])[NH2:37])[CH3:38])=[CH:28][CH:27]=1)[CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:5][O:6][C:7]1[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1012352-Bromo-2-methylpropanamideHCID 54420518HCID 54420518, compound

Product 1

HCID 54222911HCID 54222911, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium hydride (10.8 mg of a 60% dispersion in oil, 0.27 mmol) was added to a solution of the phenol prepared in example 91 (100 mg, 0.25 mmol) in dry dioxane (1 ml) and the mixture stirred for 1 h at room temperature. 2-Bromo-2-methylpropanamide (Coutts, I. G. C., Southcott, M. R. J. Chem. Soc. Perkin Trans. 1, 1990, 767) was then added and the mixture heated at 100° C. for 8 h. The reaction mixture was filtered, concentrated in vacuo, and purified by flash chromatography (1:1 ethyl acetate: hexanes) to afford a light yellow solid (94.4 mg, 94%). MS (FD+) 489.6, Mp 84-86° C.

Workup

  1. temperaturethe mixture heated at 100° C. for 8 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (1:1 ethyl acetate: hexanes)

Sources & evidence

ORD record
ord-6b607f37cf12427897026a129bb46846
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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