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

HRID 2419452Notes

Reaction equation

HRID 2419452 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 1 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-424640e6ccde49dabbb69cafc01c8530
Source dataset
uspto-grants-1978_08
Patent number
US04105776

Reaction notes

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