Acetic Acid → HCID 18317253, compound

HRID 1700124Notes

Reaction equation

HRID 1700124 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9](=[O:21])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[CH:6]=[CH:5][N:4]=1.[H-].[Na+].Cl[CH2:25][C:26]([CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH2:30][CH2:29]1)=[O:27].CC(O)=O>CS(C)=O.C([O-])([O-])=O.[Na+].[Na+]>[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9](=[O:21])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:20])[F:18])[CH:12]=2)[CH2:25][C:26](=[O:27])[CH:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[O:35])[CH2:30][CH2:29]2)[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 18317250HCID 18317250, compoundHCID 18317254HCID 18317254, compound

Product 1

HCID 18317253HCID 18317253, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

Under Ar, a solution of 25 (4.0 g, 12.8 mmol) in DMSO (30 mL) was treated with 95% NaH (0.35 g, 13.8 mmol). After stirring at room temperature for 15 min, a solution of 5 (3.9 g, 13.2 mmol) in DMSO (20 mL) was added in one portion to the deep red solution. After stirring at room temperature for 18 h, 2N AcOH was added and then poured carefully in saturated Na2CO3. The basic aqueous solution was extracted with EtOAc (3×). The organic extracts were backwashed with H2O, brine, dried, filtered and concentrated to dryness. The residue was chromatographed on a Still column (80 mm) and the product was eluted with 30% EtOAc-hexanes to yield 1.5 g of 26.

Workup

  1. stirringAfter stirring at room temperature for 18 h
  2. extractionThe basic aqueous solution was extracted with EtOAc (3×)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was chromatographed on a Still column (80 mm)
  7. washthe product was eluted with 30% EtOAc-hexanes

Sources & evidence

ORD record
ord-c117d599ad3d487a99ffcc719a0078b0
Source dataset
uspto-grants-2002_02
Patent number
US06350744B1

Reaction notes

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