HCID 131729845, compound → HCID 59479519, compound

HRID 1515544Notes

Reaction equation

HRID 1515544 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=2[C@H:16]2[C@@H:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][CH2:18][N:17]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([S:4]([CH:1]2[CH2:2][CH2:3]2)(=[O:6])=[O:5])=[C:8]([C@H:16]2[C@@H:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][CH2:18][N:17]2[C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[CH:9]=1

Participants

5

Reactant 2

HCID 131729845HCID 131729845, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59479519HCID 59479519, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 76G (2.9 g) in methanol (60 mL) was added 10% Pd/C (990 mg). The mixture was hydrogenated with a hydrogen balloon for 2.0 h. The Pd/C was removed by filtration and the filtrate was concentrated to afford 76I (2.54 g, 95% yield). 1H NMR (400 MHz, DMSO-d6, 100° C.) δ ppm 0.83-0.93 (m, 5H) 0.95-1.04 (m, 2H) 1.13-1.24 (m, 11H) 2.02-2.07 (m, 1H) 2.09-2.16 (m, 1H) 2.73-2.79 (m, 1H) 3.48-3.56 (m, 1H) 3.63-3.74 (m, 4H) 5.79 (d, J=7.70 Hz, 1H) 6.48-6.54 (m, 2H) 7.40 (d, J=8.79 Hz, 1H), LC-MS 439 (M+H).

Workup

  1. customThe Pd/C was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6afb293a2ede4a168e5656eef7f251db
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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