Water → HCID 14931303, compound

HRID 973993

Reaction equation

HRID 973993 reaction equation
[CH:1]1([C@:7]([OH:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][N:19]([CH3:25])[CH2:20][C:21]#[C:22][CH2:23][NH2:24].O>C(Cl)(Cl)Cl>[CH3:18][N:19]([CH3:25])[CH2:20][C:21]#[C:22][CH2:23][NH:24][C:8](=[O:10])[C:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 777375Cyclohexylphenylglycolic acid, (+)-HCID 12259565HCID 12259565, compound

Product 1

HCID 14931303HCID 14931303, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of (S)-(+)-2-cyclohexyl-2-hydroxy-2-phenylacetic acid (1.13 g, 80% ee) and N,N'-carbonyldiimidazole (0.77 g) in chloroform (5 ml) was stirred at room temperature for 2 hours. After an addition of 4-dimethylamino-2-butynylamine (0.54 g), the mixture was stirred at the same temperature for an additional hour, then the mixture was poured into water, and extracted with ethyl acetate. The extract was washed with water and the organic layer was extracted with 1N-hydrochloric acid. The acidic solution was adjusted to pH 13 with aqueous solution of sodium hydroxide and extracted with ethyl acetate. The extract was washed with sodium chloride aqueous solution, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (10:1) as an eluent to give (-)-N-(4-dimethylamino-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide (0.60 g, 88% ee).

Workup

  1. stirringthe mixture was stirred at the same temperature for an additional hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. extractionthe organic layer was extracted with 1N-hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with sodium chloride aqueous solution
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (10:1) as an eluent

Sources & evidence

ORD record
ord-a0ed4e33b64f471db91fd85425548675
Source dataset
uspto-grants-1991_11
Patent number
US05066680

Linked notes

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