HCID 135885194, compound → HCID 135885158, compound

HRID 2110610Notes

Reaction equation

HRID 2110610 reaction equation
C([O:8][C:9]1[CH:51]=[CH:50][C:12]([CH2:13][NH:14][C:15]2([CH2:44][CH2:45][C:46]([CH3:49])([CH3:48])[CH3:47])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([OH:25])=[C:17]([C:26]3[NH:31][C:30]4[CH:32]=[CH:33][C:34]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[CH:35][C:29]=4[S:28](=[O:42])(=[O:41])[N:27]=3)[C:16]2=[O:43])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:47][C:46]([CH3:49])([CH3:48])[CH2:45][CH2:44][C:15]1([NH:14][CH2:13][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:51][CH:50]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([OH:25])=[C:17]([C:26]2[NH:31][C:30]3[CH:32]=[CH:33][C:34]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[CH:35][C:29]=3[S:28](=[O:42])(=[O:41])[N:27]=2)[C:16]1=[O:43]

Participants

4

Reactant 1

HCID 135885194HCID 135885194, compound

Product 1

HCID 135885158HCID 135885158, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the product from Example 81 (13 mg, 0.018 mmol) and 10% Pd/C (3 mg) in methanol (1 mL) was stirred at room temperature under H2 atmosphere for 6 h. The heterogeneous solution was filtered and the filtrate was concentrated in vacuo. Column chromatography on silica (5% methanol/dichloromethane) afforded the title compound as a yellow solid (8 mg, 73%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.59-0.69 (m, 10H), 0.97-1.07 (m, 1H), 1.78-1.90 (m, 1H), 2.00-2.11 (m, 1H), 2.98 (s, 3H), 3.18 (d, J=12.21 Hz, 1H), 3.41 (d, J=12.21 Hz, 1H), 6.69 (d, J=7.93 Hz, 2H), 7.05 (d, J=8.54 Hz, 2H), 7.24 (d, J=8.54 Hz, 1H), 7.40-7.48 (m, 2H), 7.52-7.60 (m, 2H), 7.80 (d, J=7.93 Hz, 1H), 8.15 (d, J=7.32 Hz, 1H), 8.86 (s, 1H), 14.58 (s, 1H); MS m/z 639.3 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-d0a3274ef922405aaacd26de42bd203e
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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