Sodium borohydride → HCID 21893395, compound

HRID 1358655Notes

Reaction equation

HRID 1358655 reaction equation
[CH:1]([C:3]1[S:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:23])[CH2:15][NH:16][S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])=[CH:10][CH:9]=2)[CH:4]=1)=[O:2].[BH4-].[Na+]>C(O)C>[OH:2][CH2:1][C:3]1[S:7][CH:6]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:14]([CH3:23])[CH2:15][NH:16][S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])=[CH:12][CH:13]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21893521HCID 21893521, compound

Product 1

HCID 21893395HCID 21893395, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To solution of 0.09 g (0.3 mmol) of material from Example 69 in 2 mL of ethanol was added 0.01 g (0.3 mmol) of sodium borohydride. The mixture was stirred at ambient temperature for 16 hours and concentrated in vacuo. The residue was partitioned between 5 mL of ethyl acetate and 5 mL of water. The organic layer was separated and the aqueous layer was extracted three times with 3.mL each of ethyl acetate. The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Chromatography (1 g silica gel, 50% ethyl acetate/hexane) of the residue afforded 0.06 g (69%) of the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between 5 mL of ethyl acetate and 5 mL of water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted three times with 3.mL each of ethyl acetate
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2fdbfaa518c543958f8ed139aa97b193
Source dataset
uspto-grants-2003_07
Patent number
US06596716B2

Reaction notes

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