Hydrogen Sulfide → HCID 14696317, compound

HRID 1200154Notes

Reaction equation

HRID 1200154 reaction equation
[CH3:1][C:2]([NH:10][C:11](=[O:33])[C@@H:12]([NH:24][C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:13][S:14]CC1C=CC(OC)=CC=1)([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(OC)C=CC=CC=1.S>FC(F)(F)C(O)=O.CN(C)C=O>[CH3:9][C:2]([NH:10][C:11](=[O:33])[C@@H:12]([NH:24][C:25](=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:13][SH:14])([CH3:1])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 402Hydrogen SulfideHCID 7519AnisoleHCID 14696315HCID 14696315, compound

Product 1

HCID 14696317HCID 14696317, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1.010 g of (2R)-N-(α,α-dimethylbenzyl)-2-benzoylamino-3-(p-methoxybenzylthio)propionamide [prepared as described in step (a) above] was dissolved in 10 ml of trifluoroacetic acid. To this solution was added 1.0 ml of anisole and, whilst ice-cooling, this was followed by the addition of 793 mg of mercuric acetate under a nitrogen stream, and then the mixture was stirred. After stirring for 1.5 hours, the solvent was distilled off at room temperature. Diethyl ether was added to the residue and the material which separated out was filtered off. This material obtained by filtration (the mercuric salt) was dissolved in 50 ml of dimethylformamide, and, whilst ice-cooling, hydrogen sulfide gas was passed through this solution. After 1.5 hours, the mercuric sulfide which separated out was filtered off with Celite (trade mark) filter aid. The filtrate was concentrated by evaporation under reduced pressure at room temperature to give 702 mg of the title compound as crystals melting at 169°-173° C.

Workup

  1. temperaturewhilst ice-cooling
  2. stirringAfter stirring for 1.5 hours
  3. distillationthe solvent was distilled off at room temperature
  4. additionDiethyl ether was added to the residue
  5. customthe material which separated out
  6. filtrationwas filtered off
  7. customThis material obtained by filtration (the mercuric salt)
  8. temperaturewhilst ice-cooling
  9. customthe mercuric sulfide which separated out
  10. filtrationwas filtered off with Celite (trade mark)
  11. filtrationfilter aid
  12. concentrationThe filtrate was concentrated by evaporation under reduced pressure at room temperature

Sources & evidence

ORD record
ord-4ebd52c231e94d248ba3a85996f66814
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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