HCID 118098752, compound → HCID 118098753, compound

HRID 708880Notes

Reaction equation

HRID 708880 reaction equation
[C:1]([S:5]([C:8]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:9]=1[CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:24][C:21]1[CH:22]=[CH:23][C:8]([S:5]([C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:7])=[O:6])=[C:9]([CH:20]=1)[CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17]

Participants

4

Reactant 1

HCID 118098752HCID 118098752, compound

Product 1

HCID 118098753HCID 118098753, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 22A (2.5 g, 6.47 mmol) and Pd/C (0.25 g, 0.235 mmol) in MeOH (30 mL) were stirred under H2 (50 psi) overnight. The reaction was filtered and concentrated. The crude product was purified by flash chromatography (0% to 100% ethyl acetate in hexane) to yield 22B (1.6 g, 4.49 mmol, 69.4% yield) as a white solid. MS (ESI) m/z: 357.5 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.41 (1H, d, J=8.79 Hz), 6.53 (1H, d, J=8.79 Hz), 6.38 (1H, br. s.), 6.26 (2H, d, J=12.74 Hz), 4.66 (2H, s), 2.80 (3H, s), 1.29-1.56 (9H, m), 1.21 (9H, s).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customThe crude product was purified by flash chromatography (0% to 100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8355181d6afa45a38817d85aa1c3fa89
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

Loading…