Triethylamine → benzyl N-(E)-[1-oxo-2-(acetylthiomethyl)-3-phenylpropenyl]-beta-alaninate

HRID 976473Notes

Reaction equation

HRID 976473 reaction equation
[C:1]([S:4][CH2:5]/[C:6](=[CH:10]/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)/[C:7]([OH:9])=O)(=[O:3])[CH3:2].CS(O)(=O)=O.[NH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].C(N(CC)CC)C.O.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1.C(Cl)(Cl)Cl>[O:9]=[C:7]([NH:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])/[C:6](/[CH2:5][S:4][C:1](=[O:3])[CH3:2])=[CH:10]\[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 19037125Benzyl beta-alaninate methanesulphonateHCID 86750583(E)-2-acetylthiomethyl-3-phenylpropenoic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 86750582benzyl N-(E)-[1-oxo-2-(acetylthiomethyl)-3-phenylpropenyl]-beta-alaninate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

0.95 g (4 mmol) of (E)-2-acetylthiomethyl-3-phenylpropenoic acid dissolved in 15 ml of anhydrous THF is placed in a round-bottomed flask fitted with a calcium chloride guard tube. The flask is cooled to approximately 0°-5° C. in an ice bath and 1.10 g (4 mmol) of benzyl β-alaninate methanesulphonate and 0.41 g (4 mmol) of triethylamine in 5 ml of chloroform, a solution of 0.54 g (4 mmol) of hydroxybenzotriazole monohydrate in 5 ml of THF and a solution of 0.83 g (4 mmol) of dicyclohexylcarbodiimide in 5 ml of chloroform are successively added with stirring. The mixture is allowed to return to room temperature and is stirred for 6 hours.

Workup

  1. customis placed in a round-bottomed flask
  2. customfitted with a calcium chloride guard tube
  3. temperatureThe flask is cooled to approximately 0°-5° C. in an ice bath
  4. customto return to room temperature
  5. stirringis stirred for 6 hours

Sources & evidence

ORD record
ord-54740a4d081547d1ab5b69f47ca3a1ea
Source dataset
uspto-grants-1997_03
Patent number
US05612371

Reaction notes

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