HCID 137194537, compound → HCID 136384773, compound

HRID 494608Notes

Reaction equation

HRID 494608 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:15][CH2:16][CH3:17])([CH2:12][CH2:13][CH3:14])[C:4](=[O:18])[C:3]=1[C:19]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([NH:29][S:30]([NH:33]C(=O)OCC3C=CC=CC=3)(=[O:32])=[O:31])=[CH:28][C:22]=2[S:21](=[O:45])(=[O:44])[N:20]=1>CO.[Pd]>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:15][CH2:16][CH3:17])([CH2:12][CH2:13][CH3:14])[C:4](=[O:18])[C:3]=1[C:19]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([NH:29][S:30]([NH2:33])(=[O:32])=[O:31])=[CH:28][C:22]=2[S:21](=[O:44])(=[O:45])[N:20]=1

Participants

4

Reactant 1

HCID 137194537HCID 137194537, compound

Product 1

HCID 136384773HCID 136384773, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 85 (56 mg, 0.086 mmol) in 7 mL of methanol was treated with 10% palladium on carbon (28 mg, 50 wt %) and placed under an atmosphere of hydrogen. The mixture was stirred at room temp for 5 h, filtered through a 0.45 □M syringe filter, and concentrated in vacuo to afford the desired product (35 mg, 79% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.56 (m, 2H) 0.67 (m, 6H) 0.87 (m, 2H) 1.96 (m, J=11.40, 11.40 Hz, 2H) 2.16 (m, 2H) 7.37 (s, 2H) 7.59 (m, 6H) 8.15 (d, J=7.72 Hz, 1H) 9.99 (s, 1H) 13.94 (s, 1H); (ESI+) m/z 519 (M+H)+ (ESI+) m/z 536 (M+NH4)+ (ESI+) m/z 541 (M+Na)+ (ESI+) m/z 1054 (2M+NH4)+ (ESI−) m/z 517 (M−H)− (ESI−) m/z 1035 (2M−H)−

Workup

  1. filtrationfiltered through a 0.45 □M syringe
  2. filtrationfilter
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ecd5bf3d91f5470c82b1d9cd69869192
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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