Methyl iodide → HCID 13208311, compound

HRID 2419437Notes

Reaction equation

HRID 2419437 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-9bb96e51ba8e4c41b10343d0f5345690
Source dataset
uspto-grants-1978_08
Patent number
US04105776

Reaction notes

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