Sodium Hydroxide → HCID 54518968, compound

HRID 262826Notes

Reaction equation

HRID 262826 reaction equation
[C:1]([O:5][C:6](=[O:25])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:24])[CH:13]([CH2:19][C:20]([O:22]C)=[O:21])[CH2:14][S:15][C:16](=[O:18])[CH3:17])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O>[C:1]([O:5][C:6](=[O:25])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:24])[CH:13]([CH2:19][C:20]([OH:22])=[O:21])[CH2:14][S:15][C:16](=[O:18])[CH3:17])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 545040181-[3-(acetylthio)-2-methoxycarbonylmethylpropanoyl]-L-proline tert-butyl ester

Product 1

HCID 54518968HCID 54518968, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-[3-(acetylthio)-2-methoxycarbonylmethylpropanoyl]-L-proline tert-butyl ester (3.7 g) in methanol (60 ml), N sodium hydroxide (40 ml) is added. After four hours, the reaction mixture is diluted with water (100 ml) and extracted with ethyl acetate. The aqueous layer is acidified and extracted with ethyl acetate. This last ethyl acetate layer is dried and concentrated to dryness in vacuo. The residue is dissolved in a mixture of pyridine and acetic anhydride (3:1) and the solution is stored at room temperature overnight. The reaction mixture is diluted with ethyl acetate (200 ml) and washed with 10% potassium bisulfate. The organic layer is dried and concentrated to dryness in vacuo to yield 1-[3-(acetylthio)-2-carboxymethylpropanoyl]-L-proline tert-butyl ester.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialThis last ethyl acetate layer is dried
  4. concentrationconcentrated to dryness in vacuo
  5. dissolutionThe residue is dissolved in a mixture of pyridine and acetic anhydride (3:1)
  6. waitthe solution is stored at room temperature overnight
  7. additionThe reaction mixture is diluted with ethyl acetate (200 ml)
  8. washwashed with 10% potassium bisulfate
  9. customThe organic layer is dried
  10. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-cc7a8a1e367b4a8da60cb5a073bf86f1
Source dataset
uspto-grants-1979_05
Patent number
US04154960

Reaction notes

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