Acetic Acid → HCID 60205211, compound

HRID 1260222Notes

Reaction equation

HRID 1260222 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[N:18]=[CH:17][C:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])=[CH:15][CH:14]=2)[CH2:9]1)[C:2]1C=CC=C[CH:3]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl.O>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[N:18]=[CH:17][C:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:30])[CH3:31])=[CH:25][CH:24]=3)(=[O:21])=[O:22])=[CH:15][CH:14]=2)[CH2:9]1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 60205207HCID 60205207, compound

Product 1

HCID 60205211HCID 60205211, compoundYield 0%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.088 g of N-[6-(1-benzyl-pyrrolidin-3-yl)-pyridin-3-yl]-4-isopropyl-benzene-sulfonamide (0.25 mmol) were dissolved in 10 ml of dichloromethane. 0.022 g of propionyl aldehyde (0.38 mmol), 0.023 g of acetic acid (0.38 mmol) and 0.081 g of sodium triacetoxyborohydride (0.38 mmol) were added and stirred for 1 h at room temperature. Water was added, the pH adjusted to 10 with 1 N sodium hydroxide, extracted three times with ethyl acetate, the organic layers combined and evaporated to dryness. The crude material was purified via silica gel chromatography with dichloromethane/methanol 20%. Fractions containing the product were combined and the solvent evaporated to yield 0.026 mg of the product.

Workup

  1. extractionextracted three times with ethyl acetate
  2. customevaporated to dryness
  3. customThe crude material was purified via silica gel chromatography with dichloromethane/methanol 20%
  4. additionFractions containing the product
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-5906bf9896d241bc810226a500c86d1b
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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