Triethylamine → HCID 178448319, compound

HRID 1620758Notes

Reaction equation

HRID 1620758 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 866789221422130-24-2

Product 1

HCID 178448319HCID 178448319, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the crude product (19.6 g) containing N,N-dimethyl-D-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. The reaction mixture was stirred at room temperature for 3 hr, and 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) 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)

Sources & evidence

ORD record
ord-cd42e56bb169407fbec553bffa73211e
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

Loading…