Sodium borohydride → HCID 21893395, compound

HRID 380989Notes

Reaction equation

HRID 380989 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-15b197dfd9384f49a05dfd2d566ce7f0
Source dataset
uspto-grants-2001_10
Patent number
US06303816B1

Reaction notes

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