HCID 136396968, compound → HCID 136397087, compound

HRID 2110589Notes

Reaction equation

HRID 2110589 reaction equation
C([O:8][N:9]([C:13]1([CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([OH:23])=[C:15]([C:24]2[NH:29][C:28]3[CH:30]=[CH:31][C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])=[CH:33][C:27]=3[S:26](=[O:40])(=[O:39])[N:25]=2)[C:14]1=[O:41])[C:10](=[O:12])[CH3:11])C1C=CC=CC=1>CO.[Pd]>[OH:8][N:9]([C:13]1([CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([OH:23])=[C:15]([C:24]2[NH:29][C:28]3[CH:30]=[CH:31][C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])=[CH:33][C:27]=3[S:26](=[O:40])(=[O:39])[N:25]=2)[C:14]1=[O:41])[C:10](=[O:12])[CH3:11]

Participants

4

Reactant 1

HCID 136396968HCID 136396968, compound

Product 1

HCID 136397087HCID 136397087, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of Example 24B (12 mg, 0.018 mmol) and 10% Pd/C (2 mg) in methanol (1 mL) was hydrogenated at 1 atm for 1 h. The solution was filtered and the filtrate was concentrated in vacuo. Column chromatography on silica (7% methanol/dichloromethane) afforded the title compound (6 mg, 58%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.50-0.62 (m, 1H), 0.67 (dd, J=9.93, 6.62 Hz, 6H), 0.84-1.06 (m, 1H), 1.22-1.33 (m, 1H), 1.96 (s, 3H), 2.01-2.08 (m, 1H), 2.06-2.21 (m, 1H), 3.03 (s, 3H), 7.51 (m, 6H), 8.03 (d, J=8.09 Hz, 1H), 10.04 (s, 1H), 10.22 (s, 1H), 14.45-14.74 (br. s, 1H)); MS m/z 576.4 (M+H)+.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b959cf8ffbac4fcb85905a69142284e8
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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