Water → HCID 21893510, compound

HRID 1358663Notes

Reaction equation

HRID 1358663 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+].C(OCC)(=O)C.O>C(O)C>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 21893548HCID 21893548, compound

Product 1

HCID 21893510HCID 21893510, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.5 g (1.5 mmol) of material from Example 119 in 20 mL of ethyl alcohol was added 0.056 g (1.5 mmol) of sodium borohydride. The mixture was stirred at ambient temperature for 2 hr and then 10 mL of ethyl acetate and 10 mL of water was added. The organic layer was separated and the aqueous layer was extracted two times with 5 mL each of ethyl acetate. The combined-organic extracts were dried (MgSO4), filtered and concentrated in vacuo to afford 0.5 g (100%). of the title compound.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted two times with 5 mL each of ethyl acetate
  3. dry with materialThe combined-organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford 0.5 g (100%)

Sources & evidence

ORD record
ord-5183ef322df54a5a871ba885214521e2
Source dataset
uspto-grants-2003_07
Patent number
US06596716B2

Reaction notes

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