Diisopropylethylamine → HCID 178456046, compound

HRID 1620648Notes

Reaction equation

HRID 1620648 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@H:9]([C:12]#[CH:13])[CH2:10][OH:11].S=[C:15]1[CH2:19][S:18][C:17](=[O:20])[NH:16]1.C(N(C(C)C)C(C)C)C>C(O)C>[OH:11][CH2:10][C@H:9]([NH:8][C:15]1[CH2:19][S:18][C:17](=[O:20])[N:16]=1)[C:12]#[CH:13]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 86678813(R)-2-aminobut-3-yn-1-ol trifluoroacetate

Product 1

HCID 178456046HCID 178456046, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (R)-2-aminobut-3-yn-1-ol trifluoroacetate (601 mg) in ethanol (15 mL) were added 4-thioxo-1,3-thiazolidin-2-one (402 mg) and N-ethyl-N-(1-methylethyl)propan-2-amine (1.63 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 (NH, methanol/ethyl acetate), and the obtained powder was washed with ethyl acetate to give the title compound (112 mg).

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 (NH, methanol/ethyl acetate)
  5. washthe obtained powder was washed with ethyl acetate

Sources & evidence

ORD record
ord-b882f5e804dc4be8890c70a89d79d4f0
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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