Ethyl Acetate → HCID 178448361, compound

HRID 80596Notes

Reaction equation

HRID 80596 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([O:41][CH3:42])=[C:7]([CH:40]=1)[CH2:8][C@H:9]1[C:15](=[O:16])[N:14]([C:17]([NH:19][C@@H:20]([C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[C:26]([N+:33]([O-])=O)[CH:25]=2)[CH2:21][CH2:22][CH3:23])=[O:18])[CH2:13][C:12](=[N:36][O:37][CH2:38][CH3:39])[NH:11][CH2:10]1.C(OCC)(=O)C>[Zn].C(O)(=O)C>[NH2:33][C:26]1[CH:25]=[C:24]([C@H:20]([NH:19][C:17]([N:14]2[C:15](=[O:16])[C@H:9]([CH2:8][C:7]3[CH:40]=[C:3]([Cl:2])[CH:4]=[CH:5][C:6]=3[O:41][CH3:42])[CH2:10][NH:11][C:12](=[N:36][O:37][CH2:38][CH3:39])[CH2:13]2)=[O:18])[CH2:21][CH2:22][CH3:23])[CH:32]=[CH:31][C:27]=1[C:28]([OH:30])=[O:29]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 178448365HCID 178448365, compound

Product 1

HCID 178448361HCID 178448361, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To the compound 101 (2.76 g) in an ethyl acetate (32 ml) and acetic acid (16 ml) suspension, zinc powder (2.88 g) was added under ice cooling, and the mixture was stirred at that temperature for 20 minutes and at room temperature for 4 hours. The reaction mixture was filtered by a glass filter spread with Celite®, then the residue was washed with ethyl acetate (50 ml). The filtrate and the washings were combined, then the mixture was successively washed with saturated aqueous ammonium chloride solution and brine, dried over sodium sulfate, then concentrated. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate/methanol=6/6/1) to obtain the title compound (2.5 g).

Workup

  1. filtrationThe reaction mixture was filtered by a glass
  2. filtrationfilter
  3. washthe residue was washed with ethyl acetate (50 ml)
  4. washthe mixture was successively washed with saturated aqueous ammonium chloride solution and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate/methanol=6/6/1)

Sources & evidence

ORD record
ord-a1869d120dac4381af675de856e095c5
Source dataset
uspto-grants-2014_09
Patent number
US08846660B2

Reaction notes

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