HCID 131729844, compound → HCID 59479419, compound

HRID 1515543Notes

Reaction equation

HRID 1515543 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.C1COCC1.[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

6

Reactant 2

HCID 131729844HCID 131729844, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59479419HCID 59479419, compoundYield 102.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 76F (1.6 g) in methanol (40 mL) and THF (20 mL) was added 10% Pd/C (500 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 76H (1.54 g, 95% yield). 1H NMR (400 MHz, DMSO-d6, 100° C.) δ ppm 0.86-0.97 (m, 2H) 0.98-1.06 (m, 3H) 1.13-1.24 (m, 4H) 1.30 (s, 9H) 1.98 (dd, J=12.09, 8.24 Hz, 1H) 2.16 (d, J=11.54 Hz, 1H) 2.68 (s, 1H) 2.83 (d, J=7.15 Hz, 1H) 3.42 (d, J=7.15 Hz, 1H) 3.61-3.71 (m, 1H) 4.11 (q, J=7.15 Hz, 2H) 5.74 (s, 1H) 6.50-6.57 (m, 2H) 7.47 (d, J=9.34 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-f9ee104130da4e10aaa34145d1fdc569
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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