HCID 22344732, compound → HCID 22344715, compound

HRID 1059849Notes

Reaction equation

HRID 1059849 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([N+:19]([O-])=O)[CH:12]=2)[CH:6]=[C:5]([O:22][CH3:23])[C:4]=1[O:24][CH3:25]>C(O)(=O)C.ClCCl.C(OCC)(=O)C.[Zn]>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][S:9][C:7]2[CH:6]=[C:5]([O:22][CH3:23])[C:4]([O:24][CH3:25])=[C:3]([O:2][CH3:1])[CH:8]=2)=[CH:12][C:13]=1[NH2:19]

Participants

6

Reactant 1

HCID 22344732HCID 22344732, compound

Product 1

HCID 22344715HCID 22344715, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A room temperature suspension of zinc dust (2.35 g) in acetic acid (20 mL) was treated dropwise with a solution of Example 89A (100 mg, 0.27 mmol) and acetic acid (0.40 mL) in dichloromethane (1 mL), stirred at room temperature for 30 minutes, diluted with ethyl acetate (100 mL), filtered, and concentrated. The concentrate was dissolved in ethyl acetate, washed with saturated NaHCO3 and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5% ethyl acetate/dichloromethane to provide the desired product.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in ethyl acetate
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel with 5% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-48bfda42d2f741b2bdbb3b65c693ac88
Source dataset
uspto-grants-2003_02
Patent number
US06521658B1

Reaction notes

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