Diisopropylethylamine → HCID 178514014, compound

HRID 1620641Notes

Reaction equation

HRID 1620641 reaction equation
Cl.[NH2:2][C@H:3]([C:6]([NH2:8])=[O:7])[CH2:4][OH:5].S=[C:10]1[CH2:14][S:13][C:12](=[O:15])[NH:11]1.C(N(C(C)C)C(C)C)C>C(O)C>[O:15]=[C:12]1[N:11]=[C:10]([NH:2][C@H:3]([C:6]([NH2:8])=[O:7])[CH2:4][OH:5])[CH2:14][S:13]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 16212403L-Serinamide hydrochloride

Product 1

HCID 178514014HCID 178514014, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of L-serinamide hydrochloride (1.00 g) in ethanol (20 mL) were added 4-thioxo-1,3-thiazolidin-2-one (957 mg) and N-ethyl-N-(1-methylethyl)propan-2-amine (1.88 mL), and the mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (methanol/ethyl acetate), and the obtained powder was washed with ethyl acetate to give the title compound (1.09 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate)
  5. washthe obtained powder was washed with ethyl acetate

Sources & evidence

ORD record
ord-7a6597fbcde14c50a79298ed355f729f
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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