HCID 59315469, compound → HCID 59315022, compound

HRID 708808Notes

Reaction equation

HRID 708808 reaction equation
[CH:1]1([S:4]([C:7]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:8]=2[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:6])=[O:5])[CH2:3][CH2:2]1>CO.CCOC(C)=O.[Pd]>[NH2:23][C:20]1[CH:21]=[CH:22][C:7]([S:4]([CH:1]2[CH2:2][CH2:3]2)(=[O:6])=[O:5])=[C:8]([CH:19]=1)[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 1

HCID 59315469HCID 59315469, compound

Product 1

HCID 59315022HCID 59315022, compoundYield 101.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To Intermediate 8A (10.0 g, 27.0 mmol) in MeOH (250 ml) and EtOAc (150 ml) was added 10% Pd/C (0.5 g, 4.70 mmol) under a stream of nitrogen. The system was purged and degassed 3× with nitrogen, then the hydrogen balloon was introduced. The system was purged and degassed with hydrogen 3×. The mixture was stirred at rt overnight after addition of 0.5 mL of conc. HCl. The catalyst was filtered carefully over CELITE® under a stream of nitrogen and washed with methanol. The filtrate was concentrated and dried to give Intermediate 8B as an off-white solid (9.3 g). MS (ESI) (m/z) 341 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.85-1.08 (m, 4H) 1.38 (d, J=48.37 Hz, 9H) 2.67-2.78 (m, J=4.40 Hz, 1H) 2.84 (s, 3H) 4.68 (s, 2H) 5.94-6.30 (m, 2H) 6.39 (s, 1H) 7.44 (d, J=8.79 Hz, 1H).

Workup

  1. customThe system was purged
  2. customdegassed 3× with nitrogen
  3. additionthe hydrogen balloon was introduced
  4. customThe system was purged
  5. customdegassed with hydrogen 3×
  6. additionafter addition of 0.5 mL of conc. HCl
  7. filtrationThe catalyst was filtered carefully over CELITE® under a stream of nitrogen
  8. washwashed with methanol
  9. concentrationThe filtrate was concentrated
  10. customdried

Sources & evidence

ORD record
ord-562f81a5ae9f4d9a8c9b4bbc2866a4ad
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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