Sodium → 1-(2-Methyl-3-sulfanylpropanoyl)-L-proline

HRID 262576Notes

Reaction equation

HRID 262576 reaction equation
C([S:8][CH2:9][CH:10]([CH3:21])[C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])C1C=CC=CC=1.[Na].S([O-])([O-])(=O)=O.[NH4+].[NH4+]>N>[SH:8][CH2:9][CH:10]([CH3:21])[C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 6097028Ammonium SulfateHCID 21121783HCID 21121783, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent2×

Procedure

1-[3-(benzylthio)-2-methylpropanoyl]-L-proline (0.1 g.) is suspended in boiling liquid ammonia (10 ml.) and small pieces of sodium are added with stirring until persistent blue color. The color is discharged with a few crystals of ammonium sulfate and the ammonia is allowed to evaporate under a current of nitrogen. The residue is dissolved in a mixture of dilute hydrochloric acid and ethyl acetate. The organic layer is dried and 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. additionare added
  2. customto evaporate under a current of nitrogen
  3. dissolutionThe residue is dissolved in a mixture of dilute hydrochloric acid and ethyl acetate
  4. customThe organic layer is dried
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-493b6f54ca6d4f709f3089fb43a1ddb3
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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