Methanol → HCID 15056137, compound

HRID 1590487Notes

Reaction equation

HRID 1590487 reaction equation
[BH4-].[Na+].B(F)(F)F.CCOCC.[CH3:12][S:13]([O:16][C@H:17]1[CH2:21][N:20]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)=[O:23])[C@H:19]([C:35]([N:37]2[CH2:41][CH2:40][NH:39][C:38]2=[O:42])=O)[CH2:18]1)(=[O:15])=[O:14].CO>O1CCCC1.C(OCC)(=O)C>[CH3:12][S:13]([O:16][C@H:17]1[CH2:21][N:20]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)=[O:23])[C@H:19]([CH2:35][N:37]2[CH2:41][CH2:40][NH:39][C:38]2=[O:42])[CH2:18]1)(=[O:15])=[O:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 15056143(2S,4R)-4-methanesulfonyloxy-1(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine

Product 1

HCID 15056137HCID 15056137, compoundYield 41.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium borohydride (0.32 g) in tetrahydrofuran (20 ml) was added dropwise boron trifluoride etherate (6.0 ml) under ice-cooling and the mixture was stirred at the same temperature for 10 minutes. To the mixture was added a solution of (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)- 2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine (2.0 g) in tetrahydrofuran (10 ml) and the mixture was stirred at ambient temperature for 3 hours. To a reaction mixture was added dropwise methanol (30 ml) under ice-cooling and the solution was evaporated in vacuo. The resulting residue was dissolved in methanol (30 ml) and conc. hydrochloric acid (0.5 ml) and stirred overnight at ambient temperature. The reaction mixture was evaporated in vacuo to give a residue. The residue was dissolved in a mixture of ethyl acetate (60 ml) and tetrahydrofuran (30 ml) and the solution was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively, dried over anhydrous magnesium sulfate and evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (100 g) eluting with a mixture of chloroform and methanol (19:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine (0.81 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at ambient temperature for 3 hours
  3. temperaturecooling
  4. customthe solution was evaporated in vacuo
  5. dissolutionThe resulting residue was dissolved in methanol (30 ml)
  6. stirringconc. hydrochloric acid (0.5 ml) and stirred overnight at ambient temperature
  7. customThe reaction mixture was evaporated in vacuo
  8. customto give a residue
  9. washthe solution was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated in vacuo
  12. customto give a residue
  13. customThe residue was chromatographed on silica gel (100 g)
  14. washeluting with a mixture of chloroform and methanol (19:1 V/V)
  15. additionThe fractions containing the desired compound
  16. customwere collected
  17. customevaporated in vacuo

Sources & evidence

ORD record
ord-0d067301e106413981352e2fd0aabd48
Source dataset
uspto-grants-1993_04
Patent number
US05202437

Reaction notes

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