Sodium Bicarbonate → HCID 86752011, compound

HRID 727696Notes

Reaction equation

HRID 727696 reaction equation
[N:1]1([CH:6]2[CH2:11][CH2:10][N:9]([C:12]([C@@H:14]3[CH2:18][C@H:17]([S:19]CC4C=CC(OC)=CC=4)[CH2:16][N:15]3C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)=[O:13])[CH2:8][CH2:7]2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])O.[Na+]>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.C(OCC)(=O)C>[N:1]1([CH:6]2[CH2:11][CH2:10][N:9]([C:12]([C@@H:14]3[CH2:18][C@H:17]([SH:19])[CH2:16][NH:15]3)=[O:13])[CH2:8][CH2:7]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 67585037HCID 67585037, compound

Product 1

HCID 86752011HCID 86752011, compoundYield 165.1%

Reagents, catalysts & solvents 4

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolventHCID 8857Ethyl AcetateSolventHCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

1.44 g of (2S,4S)-2-[4-(imidazol-1-yl)piperidin-1-ylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (1) above] were dissolved in a mixture of 1.5 ml of anisole and 7.5 ml of trifluoroacetic acid, and 350 μl of trifluoromethanesulfonic acid were added to the resulting solution, whilst ice-cooling. The resulting mixture was then stirred at room temperature for 1 hour and then at 35° C. for 30 minutes, after which it was concentrated by evaporation under reduced pressure. The resulting residue was washed with diethyl ether four times to give a colorless powder. The whole of this powder was suspended in ethyl acetate, and the suspension was made alkaline by the addition of an aqueous solution of sodium hydrogencarbonate. The ethyl acetate phase was separated and washed with an aqueous solution of sodium chloride, after which this phase was dehydrated over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to give 1150 mg of the title compound, as a colorless powder.

Workup

  1. additionwere added to the resulting solution, whilst ice-
  2. temperaturecooling
  3. waitat 35° C. for 30 minutes
  4. concentrationafter which it was concentrated by evaporation under reduced pressure
  5. washThe resulting residue was washed with diethyl ether four times
  6. customto give a colorless powder
  7. customThe ethyl acetate phase was separated
  8. washwashed with an aqueous solution of sodium chloride
  9. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1ddbc4f7e5ab4ce7a5053d78fd0d50bb
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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