Triethylamine → HCID 178445937, compound

HRID 1620703Notes

Reaction equation

HRID 1620703 reaction equation
Cl.[CH3:2][N:3]([CH3:12])[C:4](=[O:11])[C@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[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]([CH2:7][CH:8]([CH3:9])[CH3:10])[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 86678866HCID 86678866, compound

Product 1

HCID 178445937HCID 178445937, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the crude product containing N,N-dimethyl-L-leucinamide hydrochloride (11.7 g) obtained in B) and triethylamine (18.2 g) in ethanol (150 mL) was added 4-thioxothiazolidin-2-one (8.00 g) at room temperature. The reaction mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure, and the obtained solid was suspended in THF. The suspension was filtered through celite pad and silica gel pad, and 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 (8.1 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-0a64d19ab85c43f5841f74bf09a9c39b
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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