Triethylamine → HCID 9817182, compound

HRID 1058193Notes

Reaction equation

HRID 1058193 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[C@H:5]([OH:14])[C@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:7].C(N(CC)CC)C.Cl.[C:24]1([C:30](=N)OCC)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)(=O)C.CCCCCC>ClCCCl.C(O)C>[C:24]1([C:30]2[O:14][C@@H:5]([C:4]([O:3][CH3:2])=[O:15])[C@H:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:7]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 79249Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1)HCID 21226206Ethyl acetate hexaneHCID 44475322HCID 44475322, compound

Product 1

HCID 9817182HCID 9817182, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 702EthanolSolvent

Procedure

(2R,3S)-3-Phenylisoserine methyl ester hydrochloride salt (5.76 g, 24.9 mmoles) was dissolved in 1,2-dichloroethane (75 ml). Triethylamine (2.77 g, 27.3 mmoles) was added and the resulting mixture was stirred for 15 minutes before the addition of the benzimidate prepared in step (a) above (4.62 g, 24.9 mmoles) in one portion. The mixture was stirred for 10 minutes, then heated to reflux. TLC after 4½ hours of reflux showed the reaction to be complete. (1:1 ethyl acetate/hexane, PMA/ethanol, U.V.)

Workup

  1. temperatureheated to reflux
  2. temperatureTLC after 4½ hours of reflux
  3. customthe reaction

Sources & evidence

ORD record
ord-1e22c41cefe049e881aafc2b905a5076
Source dataset
uspto-grants-2003_02
Patent number
US06515151B1

Reaction notes

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