Methyl iodide → HCID 13208311, compound

HRID 262568Notes

Reaction equation

HRID 262568 reaction equation
[CH3:1]I.C([O:5][C:6](=[O:17])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:16])[CH2:13][CH2:14][SH:15])C.[Na]>C(O)C>[CH3:1][S:15][CH2:14][CH2:13][C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:5])=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5360545SodiumHCID 53898049HCID 53898049, compound

Product 1

HCID 13208311HCID 13208311, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl iodide (71 g) is added to a solution of 1-(3-mercaptopropanoyl)-L-proline ethyl ester (115 g) and sodium (11.5 g) in ethanol (400 ml). The reaction is allowed to proceed overnight, the ethanol is removed in vacuo and the residue is dissolved in a mixture of ethyl acetate and water. The organic layer is dried and concentrated to dryness in vacuo. The resulting 1-(3-methylthiopropanoyl)-L-proline ethyl ester (98 g) is suspended in a mixture of methanol (200 ml) and 5 N sodium hydroxide (200 ml) and stirred at room temperature for five hours. The methanol is removed in vacuo, and the aqueous phase is extracted with ethyl acetate, acidified and reextracted with ethyl acetate. This last organic phase is washed with water, dried and concentrated to dryness to yield 1-(3-methylthiopropanoyl)-L-proline.

Workup

  1. customthe ethanol is removed in vacuo
  2. dissolutionthe residue is dissolved in a mixture of ethyl acetate and water
  3. customThe organic layer is dried
  4. concentrationconcentrated to dryness in vacuo
  5. additionThe resulting 1-(3-methylthiopropanoyl)-L-proline ethyl ester (98 g) is suspended in a mixture of methanol (200 ml) and 5 N sodium hydroxide (200 ml)
  6. customThe methanol is removed in vacuo
  7. extractionthe aqueous phase is extracted with ethyl acetate
  8. washThis last organic phase is washed with water
  9. customdried
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-655aeaadc09346a49e788702680ad848
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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