Sodium Hydroxide → HCID 86641054, compound

HRID 1675565Notes

Reaction equation

HRID 1675565 reaction equation
[OH-].[Na+].Cl.[OH:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[NH2:11].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]#[CH:26])[C:17](Cl)=[O:18]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[OH:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[NH:11][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:22]([O:23][CH2:24][C:25]#[CH:26])=[C:14]([O:13][CH3:12])[CH:15]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-HCID 574456713-Methoxy-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 86641054HCID 86641054, compoundYield 101.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 10 ml of a 15% aqueous sodium hydroxide solution and 20 ml of toluene were added 1.08 g of trans-2-hydroxycyclohexylamine hydrochloride, 0.05 g of tetrabutylammonium bromide and 0.80 g of 3-methoxy-4-(2-propynyloxy)benzoyl chloride, and the mixture was stirred at room temperature for 2 hours. After the reaction mixture was extracted with ethyl acetate, the organic layer was washed successively with water and an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 1.1 g of N-(trans-2-hydroxycyclohexyl)-3-methoxy-4-(2-propynyloxy)benzamide was obtained.

Workup

  1. extractionAfter the reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was washed successively with water
  3. dry with materialan aqueous saturated sodium chloride solution, dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c89dcfde6294bbb8dd53d1b3b58c572
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

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