Triethylamine → HCID 9817182, compound

HRID 2289206Notes

Reaction equation

HRID 2289206 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 4 1/2 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 4 1/2 hours of reflux
  3. customthe reaction

Sources & evidence

ORD record
ord-75159a7b4c0547b99eb3a86ba5fcb487
Source dataset
uspto-grants-2000_07
Patent number
US06090951

Reaction notes

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