Sodium Hydroxide → HCID 10670917, compound

HRID 617376Notes

Reaction equation

HRID 617376 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:32]=[CH:33][CH:34]=1)[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:31])[C@:16]([C@@H:24]2[CH2:28][CH2:27][C:26]([F:30])([F:29])[CH2:25]2)([OH:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)([O-])=O.[OH-].[Na+]>C(O)C.Cl.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:32]=[CH:33][CH:34]=1)[CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15](=[O:31])[C@:16]([C@@H:24]2[CH2:28][CH2:27][C:26]([F:30])([F:29])[CH2:25]2)([OH:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 54191238HCID 54191238, compound

Product 1

HCID 10670917HCID 10670917, compoundYield 102.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

5 mg of the (2R)-N-[1-(3-nitrobenzyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide as obtained in above step 1 was heated to 60° C. together with 2 mg of iron powder in aqueous ethanol. After adding thereto 1 drop of conc. hydrochloric acid, the heating was continued at 100° C. for about 1 hour under stirring. The reaction mixture was made basic with 4N aqueous sodium hydroxide solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to provide 4.8 mg of the title compound as a white solid.

Workup

  1. additionAfter adding
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5717b737e67f40fa9b78f3773a832fd1
Source dataset
uspto-grants-1999_09
Patent number
US05948792

Reaction notes

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