HCID 54161620, compound → HCID 53734908, compound

HRID 365499Notes

Reaction equation

HRID 365499 reaction equation
[NH2:1][C:2](=[O:33])[CH:3]([N:16]([C@@H:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:26])[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:4][C:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([F:15])=[CH:10][CH:11]=2)[CH:6]=1>CCO.[OH-].[OH-].[Pd+2]>[NH2:1][C:2](=[O:33])[CH:3]([N:16]([C@@H:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:26])[C:17](=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([F:15])=[CH:10][CH:11]=2)[CH2:6]1

Participants

4

Reactant 1

HCID 54161620HCID 54161620, compound

Product 1

HCID 53734908HCID 53734908, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2.70 g (6.10 mmol) of the compound obtained in Step 2 and 1 g of Pd(OH)2 in 120 ml of EtOH is hydrogenated under one atmosphere for 12 hours. After filtering off the catalyst, the solvent is evaporated off in vacuo. The residue obtained is chromatographed on SiO2, eluting with a solution of cyclohexane/EtOAc=40/60, to yield the title compound in the form of 2 diastereoisomers.

Workup

  1. filtrationAfter filtering off the catalyst
  2. customthe solvent is evaporated off in vacuo
  3. customThe residue obtained
  4. customis chromatographed on SiO2
  5. washeluting with a solution of cyclohexane/EtOAc=40/60

Sources & evidence

ORD record
ord-ad384b98ea6b43d381bad831b776a67a
Source dataset
uspto-grants-2000_10
Patent number
US06127396

Reaction notes

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