Pyridine → HCID 54384231, compound

HRID 1088534Notes

Reaction equation

HRID 1088534 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C@H:14]([OH:15])[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:17]1(N=C=NC2CCCCC2)CCCC[CH2:18]1.N1C=CC=CC=1.FC(F)(F)C(O)=O>CS(C)=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:14](=[O:15])[CH2:13][CH:9]1[C:10]([O:12][CH2:17][CH3:18])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 54384231HCID 54384231, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl ester of 1-t-butoxycarbonyl-L-hydroxy-proline (7.77 g) was dissolved in DMSO (30 ml), added dicyclohexylcarbodiimide (18.4 g) and 2.4 ml of pyridine and 1.2 ml of trifluoroacetic acid were added dropwise at room temperature while stirring. The mixture was stirred for two hours at that temperature, then ethyl acetate was added to the reaction mixture and insolubles were filtered off. The filtrate was washed with water, dried over Na2SO4 and distilled off the solvent used, under reduced pressure. The residue was passed through a column packed with 120 g of silica gel and eluted with benzene-ethyl acetate (98:2 v/v) and thus the objective compound was obtained (yield: 7.1 lg).

Workup

  1. additionwere added dropwise at room temperature
  2. stirringThe mixture was stirred for two hours at that temperature
  3. filtrationwere filtered off
  4. washThe filtrate was washed with water
  5. dry with materialdried over Na2SO4
  6. distillationdistilled off the solvent
  7. washeluted with benzene-ethyl acetate (98:2 v/v)
  8. customthus the objective compound was obtained (yield: 7.1 lg)

Sources & evidence

ORD record
ord-602461b6bdd14a9294f736b3aa849122
Source dataset
uspto-grants-1990_10
Patent number
US04962202

Reaction notes

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