HCID 118098697, compound → HCID 118092693, compound

HRID 708828Notes

Reaction equation

HRID 708828 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([S:6]([C:9]1[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][C:10]=1[CH2:11][N:12](C)[C:13](=O)OCC1C=CC=CC=1)(=[O:8])=[O:7])[CH3:5]>CO.[Pd]>[CH3:1][O:2][CH2:3][C@@H:4]([S:6]([C:9]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][C:10]=1[CH2:11][NH:12][CH3:13])(=[O:7])=[O:8])[CH3:5]

Participants

4

Reactant 1

HCID 118098697HCID 118098697, compound

Product 1

HCID 118092693HCID 118092693, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 6D (327 mg, 0.749 mmol) in MeOH (10 mL), was added 10% Pd—C (40 mg, 0.038 mmol). The mixture was evacuated and flushed with H2 (3×), then was stirred under an atmosphere of H2 for 7.5 h. The reaction mixture was filtered and concentrated to give 6E (203 mg, 99% yield) as a colorless semisolid. MS (ESI) m/z: 273.2 [M+1]+. 1H NMR (400 MHz, methanol-d4) δ ppm 7.58 (d, J=8.78 Hz, 1H) 6.69 (d, J=2.51 Hz, 1H) 6.64 (dd, J=8.66, 2.38 Hz, 1H) 3.78-3.89 (m, 2H) 3.59-3.67 (m, 1H) 3.44-3.55 (m, 2H) 3.21 (s, 3H) 2.37 (s, 3H) 1.28 (d, J=6.78 Hz, 3H).

Workup

  1. customThe mixture was evacuated
  2. customflushed with H2 (3×)
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7f254820878f4e9a82c59f043227f9d8
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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