Sodium borohydride → HCID 44282968, compound

HRID 413332Notes

Reaction equation

HRID 413332 reaction equation
[BH4-].[Na+].[OH:3][NH:4][C:5](=[O:34])[CH:6]([CH2:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO>[OH:3][NH:4][C:5](=[O:34])[CH:6]([CH2:16][S:17]([C:20]1[CH:21]=[CH:22][C:23]([CH:26]([OH:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:24][CH:25]=1)(=[O:18])=[O:19])[CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10389113HCID 10389113, compound

Product 1

HCID 44282968HCID 44282968, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.38 g) was added to a solution of example 58 (0.45 g) in MeOH (100 ml) and the solution was stirred for 2 h, then evaporated and the residue dissolved in water, acidified with citirc acid and extracted with ethyl acetate. The organic layer was washed with brine, dried and evaporated to give the crude product, which was purified by column chromatography, eluting with 7% MeOH in dichloromethane to give the title compound (0.43 g, 95%) as white solid.

Workup

  1. customevaporated
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. customevaporated
  7. customto give the crude product, which
  8. customwas purified by column chromatography
  9. washeluting with 7% MeOH in dichloromethane

Sources & evidence

ORD record
ord-7c728e983fe74145a63ab65ce08f61a3
Source dataset
uspto-grants-2003_05
Patent number
US06566384B1

Reaction notes

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