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

HRID 1701391Notes

Reaction equation

HRID 1701391 reaction equation
[CH3:1][CH:2]1[CH2:8][S:7][C:6](=[O:9])[C@@H:5]2[CH2:10][CH2:11][CH2:12][N:4]2[C:3]1=[O:13].CN(C)C=[O:17]>[OH-].[Na+]>[SH:7][CH2:8][CH:2]([CH3:1])[C:3]([N:4]1[CH2:12][CH2:11][CH2:10][C@H:5]1[C:6]([OH:17])=[O:9])=[O:13]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 22810363(4RS-9aS)-hexahydro-4-methyl-1H,5H-pyrrolo[2,1-c][1,4]thiazepine-1,5-dione

Product 1

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

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (4RS-9aS)-hexahydro-4-methyl-1H,5H-pyrrolo[2,1-c][1,4]thiazepine-1,5-dione (2 g) in dimethylformamide (100 ml), normal sodium hydroxide (20 ml) is added. The mixture is stirred for four hours at room temperature under argon. The solvent is removed in vacuo, the residue is dissolved in ethyl acetate and washed with 10% potassium bisulfate and water. The organic layer is dried and concentrated to yield the title compound.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with 10% potassium bisulfate and water
  4. customThe organic layer is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ecd6c521593b48eeaeadcf11041de042
Source dataset
uspto-grants-1980_03
Patent number
US04192945

Reaction notes

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