HCID 19082191, compound → HCID 19082235, compound

HRID 963554Notes

Reaction equation

HRID 963554 reaction equation
CS[CH:3]1[C:11]2[C:6](=[C:7]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:8]=[CH:9][C:10]=2[CH2:12][CH2:13][N:14]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:5][C:4]1=[O:45]>[Ni].C(O)C>[C:31]1([CH2:30][CH2:29][O:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][N:14]([CH2:13][CH2:12][C:10]2[CH:9]=[CH:8][C:7]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[C:6]3[C:11]=2[CH2:3][C:4](=[O:45])[NH:5]3)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 1

HCID 19082191HCID 19082191, compound

Product 1

HCID 19082235HCID 19082235, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney nickel (1.5 g) was added to a solution of the compound from step d) (2.1 g) in dry ethanol (60 ml). The mixture was heated to reflux for 1 hour, the catalyst was removed by filtration and the filtrate evaporated under reduced pressure. Trituration with ether gave an off-white solid which was purified by reverse phase HPLC (SiO2) using methanol:chloroform as eluant. Recrystallisation from isopropyl alcohol gave the subtitled compound as a buff coloured solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customthe catalyst was removed by filtration
  4. customthe filtrate evaporated under reduced pressure
  5. customTrituration with ether gave an off-white solid which
  6. customwas purified by reverse phase HPLC (SiO2)
  7. customRecrystallisation from isopropyl alcohol

Sources & evidence

ORD record
ord-ff6eb6b5785341d4bdc7830ad04e70ec
Source dataset
uspto-grants-1998_06
Patent number
US05763465

Reaction notes

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