D-Proline → HCID 11790498, compound

HRID 2372831Notes

Reaction equation

HRID 2372831 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].[F:9][C:10]([F:17])([F:16])[C:11](OCC)=[O:12].CN(C)C(N(C)C)=N>C1COCC1>[F:9][C:10]([F:17])([F:16])[C:11]([N:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4])=[O:12]

Participants

5

Reactant 3

HCID 8988D-Proline2×HCID 9794Ethyl trifluoroacetateHCID 664601,1,3,3-Tetramethylguanidine

Product 1

HCID 11790498HCID 11790498, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-proline (20 g, 0.174 mol) was placed in a 500 mL round-bottom flask. To this was added 100 mL THF and ethyl trifluoroacetate (50 g, 0.34 mol). The solution was purged with argon and 1,1,3,3-tetramethylguanidine (30 g, 0.261 mol) was added dropwise. The solution was allowed to stir until all the (R)-proline had dissolved (approximately 35 minutes). The solvent was removed in vacuo and the residue dissolved in CH2Cl2 (200 mL). The solution was washed with 6N HCl (aqueous, 2×100 mL). The organic layer was separated and dried with Na2SO4, filtered and the solvent removed in vacuo to give as an oil which crystallized upon standing; yield 29 g (79%), m.p. 48°-51° C.

Workup

  1. additionwas added dropwise
  2. dissolutionhad dissolved (approximately 35 minutes)
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in CH2Cl2 (200 mL)
  5. washThe solution was washed with 6N HCl (aqueous, 2×100 mL)
  6. customThe organic layer was separated
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customto give as an oil which
  11. customcrystallized

Sources & evidence

ORD record
ord-3c6d4aaf099840f894e811a9ff9dad1a
Source dataset
uspto-grants-1992_03
Patent number
US05100912

Reaction notes

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