Triethylamine → HCID 86588727, compound

HRID 1072111Notes

Reaction equation

HRID 1072111 reaction equation
[CH2:1]([O:3][C@@H:4]([C@H:9](O)[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH:23][CH3:24])[CH:17]=2)=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:2].C(N(CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([O:3][C@@H:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH:23][CH3:24])[CH:17]=2)=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86598939HCID 86598939, compound

Product 1

HCID 86588727HCID 86588727, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

19.6 g of the crude product methyl (2S,3R)-2-ethoxy-3-hydroxy-3-(3′-methylaminomethylbiphenyl-4-yl)propionate are dissolved in 200 ml of trifluoroacetic acid and 41.7 ml (297 mmol) of triethylamine are added. The reaction medium is stirred at room temperature for 48 hours and then extracted with ethyl acetate. The organic phase is decanted off, washed with a sodium hydroxide solution and then with a saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and evaporated off. The residue obtained is purified by chromatography on a silica column eluted with a dichloromethane and methanol (95/5) mixture. 1.6 g (10%) of the expected product are obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is decanted off
  3. washwashed with a sodium hydroxide solution
  4. dry with materialwith a saturated aqueous sodium chloride solution, dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated off
  7. customThe residue obtained
  8. customis purified by chromatography on a silica column
  9. washeluted with a dichloromethane and methanol (95/5) mixture

Sources & evidence

ORD record
ord-f614a7264586403e902b05c77932a47e
Source dataset
uspto-grants-2005_06
Patent number
US06908939B2

Reaction notes

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