Acetic Acid → HCID 66875450, compound

HRID 1162197Notes

Reaction equation

HRID 1162197 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[CH2:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.[S:21]1[CH:25]=[CH:24][C:23]([CH:26]=O)=[CH:22]1.[BH3-]C#N.[Na+].CC(O)=O>CO>[Cl:20][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][N:9]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[CH2:26][C:23]1[CH:24]=[CH:25][S:21][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 681353-ThiophenecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66875540HCID 66875540, compound

Product 1

HCID 66875450HCID 66875450, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate B1 (200 mg, 0.64 mmoles) was dissolved in MeOH (10 mL). Molecular sieves (4A, 200 mg) were added, and then thiophen-3-carbaldehyde (0.056 mL, 0.64 mmoles) was added. The mixture was stirred at room temperature for 2 hours, then NaBH3CN (121 mg, 1.9 mmoles) was added. AcOH was added dropwise to pH=5. After 48 hours, molecular sieves were removed by filtration, and water was added (20 mL). The mixture was extracted with AcOEt (3×50 mL), and the organic layer was washed with brine, dried over Na2SO4, and evaporated to dryness. The crude material was purified by flash chromatography (SiO2, petroleum ether/AcOEt from 9/1 to 7/3) to yield the title compound in amount of 173 mg.

Workup

  1. waitAfter 48 hours
  2. custommolecular sieves were removed by filtration, and water
  3. additionwas added (20 mL)
  4. extractionThe mixture was extracted with AcOEt (3×50 mL)
  5. washthe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customThe crude material was purified by flash chromatography (SiO2, petroleum ether/AcOEt from 9/1 to 7/3)

Sources & evidence

ORD record
ord-0aa558e6c66346a99b7b3d183282a754
Source dataset
uspto-grants-2010_10
Patent number
US07820698B2

Reaction notes

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