HCID 131729838, compound → HCID 59191776, compound

HRID 1515524Notes

Reaction equation

HRID 1515524 reaction equation
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[C@H:15]1[C@H:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:18][CH2:17][N:16]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])(=[O:5])=[O:4])[CH3:2].[H][H]>CO.C1COCC1.[Pd]>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[C:7]([C@H:15]2[C@H:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:18][CH2:17][N:16]2[C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH:8]=1

Participants

6

Reactant 2

HCID 131729838HCID 131729838, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59191776HCID 59191776, compoundYield 102.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 35E (2.2 g) in methanol (50 mL) and THF (30 mL) was added 10% Pd/C (700 mg). The mixture was hydrogenated with a hydrogen balloon for 6.0 h. The Pd/C was removed by filtration and the filtrate was concentrated to afford 35G (2.1 g, 95% yield). 1H NMR (500 MHz, DMSO-d6, 100° C.) δ ppm 1.13 (t, J=7.42 Hz, 3H) 1.16-1.23 (t, J=7.42 Hz, 3H) 1.31 (s, 9H) 1.93-2.01 (m, 1H) 2.17 (m, 1 H) 2.78 (br s, 1H) 3.14 (br s, 2H) 3.38-3.47 (m, 1H) 3.66 (t, J=8.52 Hz, 1H) 4.10 (q, J=7.42 Hz, 2H) 5.60 (s, 1H) 5.83 (br s, 1H) 6.51-6.58 (m, 2H) 7.49 (d, J=9.34 Hz, 1H); LC-MS 427 (M+H).

Workup

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

Sources & evidence

ORD record
ord-336789d239ad40c59f3d8796646be0f2
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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