Lithium borohydride → HCID 86731583, compound

HRID 1487035Notes

Reaction equation

HRID 1487035 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:10]([C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16](OC)=[O:17])(=[O:12])=[O:11].[BH4-].[Li+]>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:10]([C:13]1[CH:22]=[CH:21][CH:20]=[C:15]([CH2:16][OH:17])[CH:14]=1)(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86731584HCID 86731584, compound

Product 1

HCID 86731583HCID 86731583, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)benzoate (400 mg, 1.065 mmol) was dissolved in tetrahydrofuran (THF) (10 mL). To this solution was added lithium borohydride (2 M in THF) (0.932 mL, 1.864 mmol). The reaction was left to stir overnight, at room temperature. The reaction was quenched by the addition of 5% citric acid (10 mL), and the reaction allowed to stir under nitrogen, for 1 hour. The reaction mixture was then diluted with ethyl acetate (25 mL), and the product extracted to the organic phase. The organic phase was dried by passing it through a hydrophobic frit and then concentrated in vacuo to give the desired product, 378.7 mg. LCMS [LCMS1] Rt 1.23 min, m/z (ES+) 348 (M+H).

Workup

  1. waitThe reaction was left
  2. customThe reaction was quenched by the addition of 5% citric acid (10 mL)
  3. stirringto stir under nitrogen, for 1 hour
  4. additionThe reaction mixture was then diluted with ethyl acetate (25 mL)
  5. extractionthe product extracted to the organic phase
  6. customThe organic phase was dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78afce6f1845446fb09ee0cf72944150
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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