HCID 53716195, compound → HCID 18974140, compound

HRID 2394493Notes

Reaction equation

HRID 2394493 reaction equation
[N:1]([CH2:4][CH:5]([OH:22])[CH2:6][N:7]([CH2:18][CH:19]([CH3:21])[CH3:20])[S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])=[N+]=[N-]>CCO.[OH-].[OH-].[Pd+2]>[NH2:1][CH2:4][CH:5]([OH:22])[CH2:6][N:7]([CH2:18][CH:19]([CH3:20])[CH3:21])[S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

4

Reactant 1

HCID 53716195HCID 53716195, compound

Product 1

HCID 18974140HCID 18974140, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of Compound 24 (2.615 g, 8.011 mmol) in EtOH (20 mL) was added Pd(OH)2 /C (1.00 g). The mixture was stirred under hydrogen atmosphere for 1 day at ambient temperature. The mixture was filtered and the filtrate concentrated to yield 2.036 g (85% yield) of a colorless oil. 1H NMR (CDCl3) 0.91 (3H, d, J=6.6 Hz), 0.91 (3H, d, J=6.6 Hz), 1.91 (1H, m), 2.43 (3H, s), 2.81 (2H, m), 2.88 (1H, dd, J=13.6, 7.3 Hz), 2.95 (1H, dd, J=12.6, 7.3 Hz), 2.99 (1H, dd, J=14.5, 7.3 Hz), 3.14 (1H, dd, J=14.8, 5.3 Hz), 3.75 (1H, m), 7.31 (2H, d, J=8.4 Hz), 7.69 (2H, J=8.4 Hz).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-a070997f07eb4d5bacb683e15ac92a07
Source dataset
uspto-grants-1998_09
Patent number
US05811462

Reaction notes

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