Triethylamine → HCID 178448320, compound

HRID 1620707Notes

Reaction equation

HRID 1620707 reaction equation
Cl.[CH3:2][N:3]([CH3:11])[C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].C(N(CC)CC)C.S=[C:20]1[CH2:24][S:23][C:22](=[O:25])[NH:21]1>C(O)C>[CH3:2][N:3]([CH3:11])[C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH:6][C:20]1[CH2:24][S:23][C:22](=[O:25])[N:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 56831841N,N-Dimethyl-L-valinamide--hydrogen chloride (1/1)

Product 1

HCID 178448320HCID 178448320, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the crude product (19.6 g) containing N,N-dimethyl-L-valinamide hydrochloride obtained in B) and triethylamine (44.0 g) in ethanol (150 mL) was added 4-thioxothiazolidin-2-one (14.4 g) at room temperature, and 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, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/petroleum ether) to give the title compound (4.2 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-0f51c3273a9c472384720768bad5e06f
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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