HCID 21882791, compound → HCID 21882813, compound

HRID 722142Notes

Reaction equation

HRID 722142 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:19][CH:18]3[C:20]4([CH2:24][N:23]([CH2:25][CH2:26][CH3:27])[S:22](=[O:29])(=[O:28])[NH:21]4)[CH:15]([CH2:16][CH2:17]3)[CH2:14][C:13]=2[CH:30]=1)C1C=CC=CC=1>CO.CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:19][CH:18]3[C:20]4([CH2:24][N:23]([CH2:25][CH2:26][CH3:27])[S:22](=[O:29])(=[O:28])[NH:21]4)[CH:15]([CH2:16][CH2:17]3)[CH2:14][C:13]=2[CH:30]=1

Participants

4

Reactant 1

HCID 21882791HCID 21882791, compound

Product 1

HCID 21882813HCID 21882813, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a degassed solution of the product of Example 27 (7.6 g) in methanol/EtOAc (1:1; 300 ml) was added 10% palladium on carbon (1.3 g). The mixture was hydrogenolysed at 50 psi for 4 hrs, filtered and concentrated to give the title compound as a white foam (5.5 g). 1H NMR (d6-DMSO 360 MHz) δH 0.90 (3H, t, J=7.2), 1.03 (2H, m), 1.55 (2H, m), 1.63 (2H, m), 2.24 (2H, brm), 2.40 (2H, m), 2.87 (2H, t, J=7.1), 3.04 (1H, d, J=15.6), 3.10 (1H, d, J=15.6), 3.14 (2H, s), 6.47 (2H, m), 6.84 (1H, d, J=8), 7.60 (1H, s), 9.00 (1H, s).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4d1a1a336eed47158f3b4ee1eef409d4
Source dataset
uspto-grants-2006_11
Patent number
US07138400B2

Reaction notes

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