HCID 68609853, compound → HCID 68608088, compound

HRID 1991139Notes

Reaction equation

HRID 1991139 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[CH:11][C:12]3[CH:13]=[C:14]4[C:20]([C:21]5[CH2:22][N:23]([CH3:26])[NH:24][CH:25]=5)=[CH:19][N:18]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:15]4=[N:16][CH:17]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:20]([C:21]5[CH2:22][N:23]([CH3:26])[NH:24][CH:25]=5)=[CH:19][N:18]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[C:15]4=[N:16][CH:17]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 68609853HCID 68609853, compound

Product 1

HCID 68608088HCID 68608088, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 86 (389 mg, 0.81 mmol) in MeOH (15 mL) was added 20% Pd(OH)2 on carbon (50 mg, cat.), and the reaction mixture was stirred vigorously under H2 for 48 h. The mixture was then filtered through Celite, which was then washed with MeOH:CH2Cl2=1:1 (v/v; 200 mL). The solutions were combined and concentrated to afford 87 as a clear oil (307 mg, 0.64 mmol, 79%). 1H NMR (400 MHz, CDCl3) δ 0.00 (s, 9H), 0.99 (t, J=8.1 Hz, 2H), 1.34-1.46 (m, 2H), 1.56 (dt, J=13.9, 4.8 Hz, 2H), 1.61-2.12 (m, 5H), 2.74 (d, J=7.1 Hz, 2H), 3.64 (t, J=8.3 Hz, 2H), 4.00 (s, 4H), 4.07 (s, 3H), 5.76 (s, 2H), 7.47 (s, 1H), 7.70 (s, 1H), 7.82 (s, 1H), 7.88 (s, 1H), 8.23 (d, J=1.8 Hz, 1H).

Workup

  1. filtrationThe mixture was then filtered through Celite, which
  2. washwas then washed with MeOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3ffbd8e9e1bf4aa78084bc6d1c5da7b0
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

Loading…