HCID 58505479, compound → HCID 44236893, compound

HRID 475445Notes

Reaction equation

HRID 475445 reaction equation
[CH:1]1([C@H:7]([NH:12][C:13]([C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)=[O:14])[C:8](=[O:11])[NH:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Zn].C(O)(=O)C>[CH:1]1([C@H:7]([NH:12][C:13]([C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:13]([C:15]4[O:16][C:17]([CH3:20])=[CH:18][CH:19]=4)=[O:14])=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)=[O:14])[C:8]([NH:9][CH3:10])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 58505479HCID 58505479, compound

Product 1

HCID 44236893HCID 44236893, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

5-(4-Nitro-phenyl)-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide (760 mg, 1.96 mmol), acetic acid 15 mL and zinc (1.2 g, 19 mmol) are combined and stirred at room temperature for 30 minutes. The crude reaction mixture is filtered through celite, washed with acetonitrile and the combined washings concentrated in vacuo. The crude material is taken up in 10% methanol in DCM and washed with saturated aqueous sodium bicarbonate. The organic layer is dried, filtered and evaporated in vacuo to yield the title compound that is used without further purification, 660 mg, 94%, LC/MS ESI m/z (M+H)+=356.2.

Workup

  1. customThe crude reaction mixture
  2. filtrationis filtered through celite
  3. washwashed with acetonitrile
  4. concentrationthe combined washings concentrated in vacuo
  5. washwashed with saturated aqueous sodium bicarbonate
  6. customThe organic layer is dried
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-38e2ca3fedd34bd4b8ca713be03de481
Source dataset
uspto-grants-2014_01
Patent number
US08637550B2

Reaction notes

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