1-[3-(benzylthio)-2-methylpropanoyl]-L-proline tert. butyl ester → HCID 21121783, compound

HRID 262575Notes

Reaction equation

HRID 262575 reaction equation
C([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]([CH3:23])[CH2:14][S:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[CH2:16]([S:15][CH2:14][CH:13]([CH3:23])[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:25])=[O:5])=[O:24])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 706080431-[3-(benzylthio)-2-methylpropanoyl]-L-proline tert. butyl ester

Product 1

HCID 21121783HCID 21121783, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

1-[3-(benzylthio)-2-methylpropanoyl]-L-proline tert.butyl ester (7.8 g.) is dissolved in a mixture of anisole (55 ml.) and trifluoroacetic acid (110 ml.). After one hour storage at room temperature, the solvent is removed in vacuo and the residue is dissolved in ether, washed several times with saturated sodium chloride, dried over magnesium sulfate and evaporated to dryness in vacuo to yield 1-[3-(benzylthio)-2-methylpropanoyl]-L-proline. Rf 0.5 (Silica gel, Benzene/acetic acid 3:1) Rf 0.5. (Silica gel, Methyl-ethylketone/acetic acid/pyridine/water 14:1:2:1).

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in ether
  3. washwashed several times with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-7b71d25bae4943a6bc6c5ae03c417d7c
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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