HCID 59191786, compound → HCID 59479442, compound

HRID 1515551Notes

Reaction equation

HRID 1515551 reaction equation
[CH:1]1([S:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=2[C@H:14]2[CH:18]=[CH:17][CH2:16][N:15]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:3][CH2:2]1>CO.[Pd]>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([S:4][CH:1]2[CH2:2][CH2:3]2)=[C:6]([C@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:7]=1

Participants

4

Reactant 1

HCID 59191786HCID 59191786, compound

Product 1

HCID 59479442HCID 59479442, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

85F (1.52 g, 4.19 mmol) and 10% Pd/C (560 mg) in MeOH (100 mL) was hydrogenated under 45 psi for 3.5 h. TLC and LC-MS indicate a clean conversion to the product. Pd/C was removed by filtration through a pad of Celite®. The filtrate was concentrated to give 85G (1.37 g, 97% yield) as a solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 0.52-0.64 (m, 2H) 0.85-0.95 (m, 2H) 1.16-1.24 (s, 7H) 1.45 (s, 2H) 1.71 (m, 1H) 1.82-1.94 (m, 2H) 2.09-2.19 (m, 1H) 2.32 (m, 1H) 3.47-3.57 (m, 1H) 3.59-3.69 (m, 1H) 5.18-5.25 (m, 1H) 6.48 (d, J=2.20 Hz, 1H) 6.58 (dd, J=8.13, 2.42 Hz, 1H) 7.30 (t, J=8.35 Hz, 1H), LC-MS 235 (M-Boc).

Workup

  1. customPd/C was removed by filtration through a pad of Celite®
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-818b7fffd81f41f7ae0fba350e03ca9d
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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