Hydrochloric Acid → (2S,4S)-1-methyl-2-aminocarbonyl-4-mercaptopyrrolidine hydrochloride

HRID 2371394Notes

Reaction equation

HRID 2371394 reaction equation
[CH3:1][N:2]1[CH2:6][C@@H:5]([S:7]C(=O)C)[CH2:4][C@H:3]1[C:11]([NH2:13])=[O:12].C[O-].[Na+].[ClH:17]>CO>[ClH:17].[CH3:1][N:2]1[CH2:6][C@@H:5]([SH:7])[CH2:4][C@H:3]1[C:11]([NH2:13])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 56626958(2S,4S)-1-methyl-2-aminocarbonyl-4-acetylthiopyrrolidine

Product 1

HCID 86745514(2S,4S)-1-methyl-2-aminocarbonyl-4-mercaptopyrrolidine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(2S,4S)-1-Methyl-2-aminocarbonyl-4-acetylthiopyrrolidine (201 mg) was dissolved in methanol (2.4 ml), and a solution of sodium methoxide (54 mg) in methanol (1.2 ml) was added thereto at room temperature under nitrogen stream, followed by stirring at the same temperature for 5 minutes. To the reaction mixture, conc. hydrochloric acid (240 mg) was added, and the solvent was removed. The residue was dissolved in a mixture of chloroform and methanol (4:1) and dried over magnesium sulfate. Removal of the solvent gave (2S,4S)-1-methyl-2-aminocarbonyl-4-mercaptopyrrolidine hydrochloride.

Workup

  1. customat room temperature
  2. customthe solvent was removed
  3. dissolutionThe residue was dissolved in a mixture of chloroform and methanol (4:1)
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-24be3b636afc49509183186082df5049
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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