HCID 178456088, compound → HCID 178456089, compound

HRID 80584Notes

Reaction equation

HRID 80584 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:44][CH3:45])=[C:6]([CH:43]=1)[CH2:7][C@@H:8]1[CH2:14][NH:13][C:12](=[N:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][N:10]([C:23]([NH:25][C@@H:26]([C:29]2[O:30][CH:31]=[C:32]([C:34]([O:36]CC(Cl)(Cl)Cl)=[O:35])[N:33]=2)[CH2:27][CH3:28])=[O:24])[C:9]1=[O:42]>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:44][CH3:45])=[C:6]([CH:43]=1)[CH2:7][C@H:8]1[C:9](=[O:42])[N:10]([C:23]([NH:25][C@@H:26]([C:29]2[O:30][CH:31]=[C:32]([C:34]([OH:36])=[O:35])[N:33]=2)[CH2:27][CH3:28])=[O:24])[CH2:11][C:12](=[N:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:13][CH2:14]1

Participants

4

Reactant 1

HCID 178456088HCID 178456088, compound

Product 1

HCID 178456089HCID 178456089, compoundYield 23.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To the compound 61a obtained in Step (1) (90 mg) was dissolved in acetic acid (2 ml), zinc powder (180 mg) was added, and the mixture was stirred at room temperature for 3 hours. The insolubles were filtered out, then the filtrate was concentrated, and the residue was purified by preparative thin layer chromatography (silica gel, chloroform/methanol/acetic acid=8/1/0.25) to obtain the title compound (17.4 mg).

Workup

  1. filtrationThe insolubles were filtered out
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by preparative thin layer chromatography (silica gel, chloroform/methanol/acetic acid=8/1/0.25)

Sources & evidence

ORD record
ord-1ac8e8fe0b954362835128b951921550
Source dataset
uspto-grants-2014_09
Patent number
US08846660B2

Reaction notes

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