HCID 58505075, compound → HCID 58505252, compound

HRID 1944912Notes

Reaction equation

HRID 1944912 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:17]=[C:18]([S:22]([C:25]3[CH:26]=[C:27]4[C:32](=[C:33]([CH3:35])[CH:34]=3)[N:31]=[CH:30][C:29]([C:36]([NH2:38])=[O:37])=[C:28]4[NH:39][C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH3:47])[CH:41]=3)(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=2)=[O:15])=[CH:9][CH:8]=1>CO.C1COCC1.[OH-].[OH-].[Pd+2]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14]([C:16]2[CH:17]=[C:18]([S:22]([C:25]3[CH:26]=[C:27]4[C:32](=[C:33]([CH3:35])[CH:34]=3)[N:31]=[CH:30][C:29]([C:36]([NH2:38])=[O:37])=[C:28]4[NH:39][C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH3:47])[CH:41]=3)(=[O:23])=[O:24])[CH:19]=[CH:20][CH:21]=2)=[O:15])=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 58505075HCID 58505075, compound

Product 1

HCID 58505252HCID 58505252, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Pd(OH)2 (20% on activated carbon, 250 mg) was added to a solution of Intermediate 72 (250 mg, 0.38 mmol) in MeOH/THF (1:1) (10 mL). The solution was hydrogenated via balloon for 5 h. The Pd was filtered through a plug of celite. The filtrate was then concentrated in vacuo to afford the title compound as a yellow solid (260 mg). ES/MS calcd. for C36H37N4O6S+ 653.2. Found m/z=653.3 (M+H)+.

Workup

  1. filtrationThe Pd was filtered through a plug of celite
  2. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-2a4d2c53e34448578b33d431c442780b
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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