HCID 54300022, compound → HCID 53919388, compound

HRID 343910Notes

Reaction equation

HRID 343910 reaction equation
C1(S[C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][C@H:18]4[CH2:22][O:21][C:20](=[O:23])[NH:19]4)[CH:15]=3)[NH:10][CH:9]=2)C=CC=CC=1>[Ni].CC(O)C>[O:23]=[C:20]1[NH:19][C@@H:18]([CH2:17][C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][CH:9]=[CH:8]3)[CH2:22][O:21]1

Participants

4

Reactant 1

HCID 54300022HCID 54300022, compound

Product 1

HCID 53919388HCID 53919388, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 3776IsopropanolSolvent

Procedure

Raney nickel (3.0 g) was added to a solution of the product from step (a) (3.1 g) in IPA (150 ml) and the suspension refluxod for 1 hour. More Raney nickel (2.0 g) was added and refluxing continued for a further 2 hours. The suspension was filtered hot through Hyflo and the filtrate evaporated in vacuo to give an oil. The latter was eluted through a silica column using ethyl acetate as eluant to give the desired product as a froth (1.3 g). 1H NMR and MS were consistent with the proposed structure.

Workup

  1. temperaturerefluxing
  2. waitcontinued for a further 2 hours
  3. filtrationThe suspension was filtered hot through Hyflo
  4. customthe filtrate evaporated in vacuo
  5. customto give an oil
  6. washThe latter was eluted through a silica column

Sources & evidence

ORD record
ord-6941ae61f1074ffc8ac4cd516ce00bad
Source dataset
uspto-grants-1999_01
Patent number
US05863935

Reaction notes

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