Ethanol → HCID 68687667, compound

HRID 2245338Notes

Reaction equation

HRID 2245338 reaction equation
[H-].[Na+].C(O[C:6](=[O:27])[CH2:7][CH2:8][N:9]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10](=[O:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C.CCO>CCOCC>[CH2:19]([N:9]1[CH2:8][CH2:7][C:6](=[O:27])[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10]1=[O:18])[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 68688317HCID 68688317, compound

Product 1

HCID 68687667HCID 68687667, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium hydride (1.1 g, 50% in mineral oil) was suspended in ether (40 ml) under argon at RT. 3-(Phenethyl-phenylacetyl-amino)-propionic acid ethyl ester (2.5 g) was added in portions followed by addition of abs. EtOH (0.5 ml). The resulting mixture was refluxed for 2 hours, cooled and poured into water/ice/1 N HCl. The aqueous layer was extracted with ethyl acetate and the organic layer was separated, washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (ethyl acetate/hexanes 1:1 and then DCM/MeOH 95:5) to give the desired product as a light yellow foam (801 mg). MS (ESI: 294.4 (MH+).

Workup

  1. additionfollowed by addition of abs
  2. temperatureThe resulting mixture was refluxed for 2 hours
  3. temperaturecooled
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. customthe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash chromatography (ethyl acetate/hexanes 1:1

Sources & evidence

ORD record
ord-99fcdb4f513a41a8b678cdd8443ab8d1
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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