HCID 66971274, compound → HCID 66971018, compound

HRID 1361330Notes

Reaction equation

HRID 1361330 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:22](=[O:28])[C:23]([C:26]#[N:27])([CH3:25])[CH3:24])[CH:14]2[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:29]([N:31]([CH3:33])[CH3:32])=[O:30])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H][H]>CO.[Pd]>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:22](=[O:28])[C:23]([CH3:24])([CH3:25])[CH2:26][NH2:27])[CH:14]2[CH2:19][CH2:18][C:17]([CH3:20])([CH3:21])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:29]([N:31]([CH3:32])[CH3:33])=[O:30])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 66971274HCID 66971274, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66971018HCID 66971018, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-BOC-(2S,4S)-4-[(2-cyano-2-methylpropanoyl)(4,4-dimethylcyclohexyl)amino]-2-[(dimethylamino)carbonyl]pyrrolidine (1.07 g, 2.31 mmol) prepared in Step A in methanol was added Pd/C (9 mg), and carried out hydrogen reaction at rt for 10 h. After the reaction finished, the reaction mixture was filtered through Celite, and the filtrate was concentrated in vacuo, and purified by HPLC to give the title compound (0.84 g, 78%).

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-b770cb3f178d4da69d33027762cce9cf
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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