1-(4-methoxycarbonyl-2-methylbutanoyl)-L-proline tert.-butyl ester → 1-(4-Methoxycarbonyl-2-methylbutanoyl)-L-proline

HRID 262753Notes

Reaction equation

HRID 262753 reaction equation
C([O:5][C:6](=[O:22])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:21])[CH:13]([CH3:20])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])(C)(C)C>FC(F)(F)C(O)=O>[CH3:19][O:18][C:16]([CH2:15][CH2:14][CH:13]([CH3:20])[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:22])=[O:5])=[O:21])=[O:17]

Participants

3

Reactant 1

HCID 706097971-(4-methoxycarbonyl-2-methylbutanoyl)-L-proline tert.-butyl ester

Product 1

HCID 541271821-(4-Methoxycarbonyl-2-methylbutanoyl)-L-proline

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-(4-Methoxycarbonyl-2-methylbutanoyl)-L-proline tert.-butyl ester (3.4 g.) is dissolved in trifluoroacetic acid (25 ml.) and the solution kept at room temperature for one hour. The trifluoroacetic acid is removed in vacuo and the residue is reprecipitated from ethyl-hexane several times. The residue is dissolved in acetonitrile (12 ml.) and 2 ml. of dicyclohexylamine is added. The crystalline salt is isolated by filtration and recrystallized from acetonitrile to yield 18 g. of 1-(4-methoxycarbonyl-2-D-methylbutanoyl)-L-proline dicyclohexylamine salt, m.p. 174°-175°. From the mother liquors the 1-(4-methoxycarbonyl-2-L-methylbutanoyl)-L-proline isomer is also separated as the dicyclohexylamine salt. The salts are converted to the acids by treatment with Dowex 50.

Workup

  1. customThe trifluoroacetic acid is removed in vacuo
  2. customthe residue is reprecipitated from ethyl-hexane several times
  3. dissolutionThe residue is dissolved in acetonitrile (12 ml.)
  4. additionof dicyclohexylamine is added
  5. customThe crystalline salt is isolated by filtration
  6. customrecrystallized from acetonitrile
  7. customto yield 18 g
  8. customis also separated as the dicyclohexylamine salt

Sources & evidence

ORD record
ord-53641a4cf92042419ceae418aadcb0a0
Source dataset
uspto-grants-1979_05
Patent number
US04154937

Reaction notes

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