Acetic Acid → HCID 59302552, compound

HRID 2237451Notes

Reaction equation

HRID 2237451 reaction equation
[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6][C:5]=2[S:4][C:3]=1CC1C(F)=CC=CC=1Cl.O.[C:22]([O-:25])(O)=[O:23].[Na+].[CH3:27][C:28](O)=O>[Zn]>[CH2:27]([O:25][C:22]([N:8]1[CH2:9][CH2:10][C:11]2[C:2]([Br:1])=[CH:3][S:4][C:5]=2[CH2:6][CH2:7]1)=[O:23])[CH3:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 11624973HCID 11624973, compound

Product 1

HCID 59302552HCID 59302552, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
22 °C

Procedure

A solution of the product from example 3, step a) (148 mg, 0.39 mmol) in AcOH (80 μl) and H2O (1.92 ml) was treated with Zn (76 mg, 1.17 mmol) at 105° C. for 4.5 hours. Next, the contents were cooled to 22° C., poured into sat. NaHCO3 (25 ml) and extracted with EtOAc (2×25 ml). The organic layer was dried (MgSO4) and concentrated providing 80 mg (68%) of the subtitle compound, which was used without further purification.

Workup

  1. extractionextracted with EtOAc (2×25 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0b0f533023cd4915829c6943fd67bffd
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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