HCID 23286159, compound → HCID 23286165, compound

HRID 1637379Notes

Reaction equation

HRID 1637379 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH2:8][C:9]12[CH:20]3[CH2:21][C:16]([CH:28]=[O:29])([C:17]1([C:25]([O-:27])=[O:26])[C:18]([CH:22]([CH3:24])[CH3:23])=[CH:19]3)[CH:15]1[CH:11]([CH:12]([CH3:30])[CH2:13][CH2:14]1)[CH2:10]2)=[O:6])=[N+]=[N-].[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH2:1][CH2:4][C:5]([O:7][CH2:8][C:9]12[CH:20]3[CH2:21][C:16]([CH:28]=[O:29])([C:17]1([C:25]([OH:27])=[O:26])[C:18]([CH:22]([CH3:24])[CH3:23])=[CH:19]3)[CH:15]1[CH:11]([CH:12]([CH3:30])[CH2:13][CH2:14]1)[CH2:10]2)=[O:6]

Participants

5

Reactant 2

HCID 23286159HCID 23286159, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23286165HCID 23286165, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The azide obtained above was dissolved in methanol and palladium hydroxide on carbon was added. The reaction was stirred under one atmosphere of hydrogen for a time sufficient to remove the benzyl ester group and reduce the azide. Concentration under reduced pressure gave the title compound. 1H NMR (CD3OD): δ0.77 (3H, d, J=6.4), 0.93 (3H, d, J=6.7), 0.94 (3H, d, J=6.6), 1.50-2.30 (11H, m), 2.36 (1H, m), 2.51 (1H, m), 3.60-4.60 (4H, m), 5.90 (1H, s), 9.81 (1H, s).

Workup

  1. customto remove the benzyl ester group
  2. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-2d8a3c0d8b894439bbf823c83b42b8a3
Source dataset
uspto-grants-2000_03
Patent number
US06040463

Reaction notes

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