Triethylamine → HCID 178472676, compound

HRID 1620626Notes

Reaction equation

HRID 1620626 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.S=[C:17]1[CH2:21][S:20][C:19](=[O:22])[NH:18]1>C(O)C>[O:22]=[C:19]1[N:18]=[C:17]([NH:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:21][S:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 178472676HCID 178472676, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl glycinate hydrochloride (5.00 g) and triethylamine (4.99 mL) in ethanol (60 mL) was added 4-thioxo-1,3-thiazolidin-2-one (3.98 g), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.84 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-48f51984391749a6a300a5b18cd43b44
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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