Triethylamine → HCID 131726679, compound

HRID 1592980Notes

Reaction equation

HRID 1592980 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](CNC)[CH:17]=2)=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:2].[CH2:26]([N:28](CC)[CH2:29]C)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:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][C:11]=1[CH2:26][NH:28][CH3:29])[C:5]([O:7][CH3:8])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86598939HCID 86598939, compound

Product 1

HCID 131726679HCID 131726679, 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-0249489bf5e04701b8ef5d248e869e62
Source dataset
uspto-grants-2007_11
Patent number
US07294639B2

Reaction notes

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