Triethylamine → HCID 178455892, compound

HRID 1620705Notes

Reaction equation

HRID 1620705 reaction equation
Cl.[CH3:2][N:3]([CH3:12])[C:4](=[O:11])[C@H:5]([C@H:7]([CH2:9][CH3:10])[CH3:8])[NH2:6].C(N(CC)CC)C.S=[C:21]1[CH2:25][S:24][C:23](=[O:26])[NH:22]1>C(O)C>[CH3:12][N:3]([CH3:2])[C:4](=[O:11])[C@H:5]([C@H:7]([CH2:9][CH3:10])[CH3:8])[NH:6][C:21]1[CH2:25][S:24][C:23](=[O:26])[N:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 86678869HCID 86678869, compound

Product 1

HCID 178455892HCID 178455892, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the crude product (19.4 g) containing N,N-dimethyl-L-isoleucinamide hydrochloride obtained in B) and triethylamine (49.5 g) in ethanol (150 mL) was added 4-thioxothiazolidin-2-one (16.3 g) at room temperature. The reaction mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure, the obtained solid was suspended in THF, and the suspension was filtered through celite pad and silica gel pad. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/petroleum ether) to give the title compound (6.2 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. filtrationthe suspension was filtered through celite pad and silica gel pad
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-8f609b7ded4a4e42aed5e18b5672cff7
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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