Hydrogen Sulfide → 1-(2-Methyl-3-sulfanylpropanoyl)-L-proline

HRID 262583Notes

Reaction equation

HRID 262583 reaction equation
C(NC[S:6][CH2:7][CH:8]([CH3:19])[C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])(=O)C.S>C(O)(=O)C.O>[SH:6][CH2:7][CH:8]([CH3:19])[C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10]

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 54264443HCID 54264443, compound

Product 1

HCID 128775471-(2-Methyl-3-sulfanylpropanoyl)-L-proline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1-[3-(acetamidomethylthio)-2-methylpropanoyl]-L-proline (1.4 g.) and mercuric acetate (1.93 g.) are dissolved in a mixture of acetic acid (25 ml.) and water (25 ml.). After one hour stirring on the steam bath, hydrogen sulfide is bubbled through until no more precipitation of mercuric sulfide is observed. The mixture is filtered, the precipitate is washed with ethanol, and the filtrate is concentrated to dryness in vacuo to yield 1-(3-mercapto-2-methylpropanoyl)-L-proline. Rf : 0.35 (Silica gel, Benzene/Acetic acid 3:1); Rf : 0.5 (Silica gel, Methyl-ethylketone/Acetic acid/pyridine/water 14:1:2:1) identical to the compound of Example 34.

Workup

  1. customis bubbled through until no more precipitation of mercuric sulfide
  2. filtrationThe mixture is filtered
  3. washthe precipitate is washed with ethanol
  4. concentrationthe filtrate is concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-785a2cc4088b42a99da33305790e9dc9
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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