Sodium borohydride → HCID 15895427, compound

HRID 1637709Notes

Reaction equation

HRID 1637709 reaction equation
[CH3:1][C:2]1[C:3]([N:8]([CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:20][C:19]=3[CH:29]=[O:30])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[N:4][O:5][C:6]=1[CH3:7].[BH4-].[Na+]>CO>[CH3:1][C:2]1[C:3]([N:8]([CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:20][C:19]=3[CH2:29][OH:30])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[N:4][O:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15895425HCID 15895425, compound

Product 1

HCID 15895427HCID 15895427, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the title product of Step D of Example 1 (0.37 g, 0.76 mmol) in 10 mL of MeOH at room temperature, sodium borohydride (0.035 g, 0.93 mmol) was added and the mixture stirred for 2 hours. The clear solution was then concentrated to 5 mL and diluted with 100 mL of water and the aqueous solution was extracted with 3×100 mL of EtOAc. The combined organic extracts were then washed once with water and dried and evaporated to provide 0.36 g (95%) of the title product of this step as a colorless gum. Rf (silica gel)=0.32 (5% methanol in CH2Cl2).

Workup

  1. concentrationThe clear solution was then concentrated to 5 mL
  2. additiondiluted with 100 mL of water
  3. extractionthe aqueous solution was extracted with 3×100 mL of EtOAc
  4. washThe combined organic extracts were then washed once with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-83106aef68ca4d74b13d26ef2494cd2c
Source dataset
uspto-grants-2000_03
Patent number
US06043265

Reaction notes

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