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

HRID 65712Notes

Reaction equation

HRID 65712 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-7f533fadaa4d4ac68b417529015fe1cd
Source dataset
uspto-grants-1978_12
Patent number
US04128653

Reaction notes

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