HCID 67223097, compound → HCID 67221778, compound

HRID 876568Notes

Reaction equation

HRID 876568 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:30])[C@H:11]([OH:29])[C@H:12]2[O:17][CH2:16][CH2:15][N:14]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([N+:25]([O-])=O)[CH:19]=3)[C:13]2=[O:28])=[CH:5][CH:4]=1)#[N:2]>C(O)(C)=O.O.[Fe]>[NH2:25][C:20]1[CH:19]=[C:18]([N:14]2[CH2:15][CH2:16][O:17][C@H:12]([C@@H:11]([OH:29])[C:10]([NH:9][C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[O:30])[C:13]2=[O:28])[CH:23]=[CH:22][C:21]=1[CH3:24]

Participants

4

Reactant 1

HCID 67223097HCID 67223097, compound

Product 1

HCID 67221778HCID 67221778, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

To a solution of compound 9-4 (70 mg) in AcOH—H2O (2 mL-0.1 mL), was added electrolytic iron powder (95.3 mg). The reaction mixture was stirred at room temperature for 1 hour then at 40° C. for 2 hours to complete the reaction. The reaction mixture was filtered with Celite® pad to remove iron powder. The filtrate was concentrated in vacuo. The resulting residue was purified by amino-silica gel flash column chromatography (eluent: CH2Cl2/MeOH=98/2-95/5) to obtain compound 9-5 (30 mg) as a colorless amorphous solid.

Workup

  1. waitat 40° C. for 2 hours to complete
  2. customthe reaction
  3. filtrationThe reaction mixture was filtered with Celite® pad
  4. customto remove iron powder
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe resulting residue was purified by amino-silica gel flash column chromatography (eluent: CH2Cl2/MeOH=98/2-95/5)

Sources & evidence

ORD record
ord-e532308a6b5c4986acc41b4843fc5ee3
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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