1-(2-ethoxycarbonylpropanoyl)-L-proline tert.-butyl ester → 1-(2-ethoxycarbonylpropanoyl)-L-proline

HRID 262747Notes

Reaction equation

HRID 262747 reaction equation
C([O:5][C:6](=[O:21])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:20])[CH:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:14])(C)(C)C>FC(F)(F)C(O)=O>[CH2:18]([O:17][C:15]([CH:13]([CH3:14])[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:21])=[O:5])=[O:20])=[O:16])[CH3:19]

Participants

3

Reactant 1

HCID 706103371-(2-ethoxycarbonylpropanoyl)-L-proline tert.-butyl ester

Product 1

HCID 536785471-(2-ethoxycarbonylpropanoyl)-L-proline

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The ester obtained in Example 2 (5.9 g.) is dissolved in trifluoroacetic acid, the solution is kept at room temperature for one hour, and then concentrated to dryness in vacuo. The residue is dissolved in a mixture of ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous phase is acidified and extracted with ethyl acetate. The ethyl acetate layer is dried over magnesium sulfate and concentrated to dryness in vacuo to obtain 1-(2-ethoxycarbonylpropanoyl)-L-proline, yield 4.1 g.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. dissolutionThe residue is dissolved in a mixture of ethyl acetate and saturated aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer is dried over magnesium sulfate
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-1e831c37c70f42c6ba23fd704ea7e7fe
Source dataset
uspto-grants-1979_05
Patent number
US04154937

Reaction notes

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