Methanol → HCID 53918022, compound

HRID 620788Notes

Reaction equation

HRID 620788 reaction equation
[BH4-].[Na+].B(F)(F)F.CCOCC.[CH2:12]([O:19][C:20]([N:22]1[CH2:26][C@H:25]([O:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][C@H:23]1[CH2:32][O:33][CH2:34][C:35]([NH:37][C:38]([NH2:40])=[O:39])=O)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CO>O1CCCC1>[CH2:12]([O:19][C:20]([N:22]1[CH2:26][C@H:25]([O:27][S:28]([CH3:31])(=[O:29])=[O:30])[CH2:24][C@H:23]1[CH2:32][O:33][CH2:34][CH2:35][NH:37][C:38]([NH2:40])=[O:39])=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 53930560HCID 53930560, compound

Product 1

HCID 53918022HCID 53918022, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium borohydride (0.1 g) in tetrahydrofuran (10 ml) was added boron trifluoride etherate (0.3 ml) with stirring at 0°-10° C. After 30 minutes, a solution of (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxy-2- [(ureidocarbonylmethyl)oxymethyl]pyrrolidine (0.63 g) in tetrahydrofuran (5 ml) was added to the mixture at 0°-10° C. The mixture was stirred at the same condition for 2 hours and at ambient temperature for 15 hours. Methanol (5 ml) was added to the mixture at 0°-10° C. The mixture was stirred at ambient temperature for 3 hours and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (25 g) and eluted with a mixture of methanol and chloroform (2:98 V/V) to give (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxy-2-[(2-ureidoethyl)oxymethyl]pyrrolidine (0.24 g).

Workup

  1. stirringThe mixture was stirred at the same condition for 2 hours and at ambient temperature for 15 hours
  2. stirringThe mixture was stirred at ambient temperature for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. customto give a syrup
  5. washeluted with a mixture of methanol and chloroform (2:98 V/V)

Sources & evidence

ORD record
ord-7bbfe0fa0f0b43bbaedd3be1cfba9af2
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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