Dichloromethane → HCID 59128675, compound

HRID 1991136Notes

Reaction equation

HRID 1991136 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([CH:20]=[C:21]([CH3:23])[CH3:22])[CH:18]=3)[N:13]([S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:12]=2)[N:10]=1)=[O:5])[CH3:2].C(Cl)Cl>CO.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH:18]=3)[N:13]([S:24]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)(=[O:26])=[O:25])[CH:12]=2)[N:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 59128697HCID 59128697, compound

Product 1

HCID 59128675HCID 59128675, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 80 (548 mg, 1.32 mmol) in MeOH:CH2Cl2=3:1 (v/v; 20 mL) was added 20% Pd(OH)2 on carbon (100 mg, cat.), and the reaction mixture was stirred vigorously under H2 for 72 h. The mixture was then filtered through Celite, which was then washed with MeOH:CH2Cl2=1:1 (v/v; 100 mL). The solutions were combined and concentrated to afford 81 as a foam (412 mg, 0.99 mmol, 75%). 1H NMR (400 MHz, CDCl3) δ 0.84 (d, J=6.6 Hz, 2H), 1.40 (t, J=7.1 Hz, 3H), 1.82 (nonet, J=6.7 Hz, 1H), 2.51 (d, J=7.2 Hz, 2H), 4.45 (q, J=7.1 Hz, 2H), 7.41 (t, J=7.8 Hz, 2H), 7.48 (t, J=7.6 Hz, 1H), 7.66 (s, 1H), 8.03 (d, J=1.8 Hz, 1H), 8.15 (d, J=7.5 Hz, 1H), 8.20 (s, 1H), 8.22 (d, J=1.9 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-4dfc7a5381c34f9e8240636f754a5e86
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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