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

HRID 65718Notes

Reaction equation

HRID 65718 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-66961288e8e5454eb14fad6b7084ced1
Source dataset
uspto-grants-1978_12
Patent number
US04128653

Reaction notes

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