HCID 22490251, compound → HCID 22490283, compound

HRID 2180020Notes

Reaction equation

HRID 2180020 reaction equation
C(OC([NH:11][CH:12]([CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=1)[CH2:13][N:14]1[CH2:21][CH:20]2[CH:22]([OH:23])[CH:16]([CH2:17][N:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]2)[CH2:15]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][CH:12]([CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=1)[CH2:13][N:14]1[CH2:21][CH:20]2[CH:22]([OH:23])[CH:16]([CH2:17][N:18]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:19]2)[CH2:15]1

Participants

4

Reactant 1

HCID 22490251HCID 22490251, compound

Product 1

HCID 22490283HCID 22490283, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23938PalladiumSolvent

Procedure

tert-Butyl 7-[2-{[(benzyloxy)carbonyl]amino}-3-(4-cyanophenoxy)propyl]-9-hydroxy-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (from step (i) above; 6.17 g; 11.2 mmol) was dissolved in ethanol (56 mL; 85%) and hydrogenated over Pd/C (5%). The resultant mixture was filtered, the solvent was evaporated and the crude product was purified by chromatography on silica (toluene:ethyl acetate:isopropanol; 8:1:1) which gave 2.99 g (64%) of the tide compound.

Workup

  1. filtrationThe resultant mixture was filtered
  2. customthe solvent was evaporated
  3. customthe crude product was purified by chromatography on silica (toluene:ethyl acetate:isopropanol; 8:1:1) which

Sources & evidence

ORD record
ord-7c2df9cfb0194abea2c43410b4d0edb7
Source dataset
uspto-grants-2005_05
Patent number
US06887881B1

Reaction notes

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