HCID 54266376, compound → HCID 54425267, compound

HRID 1636882Notes

Reaction equation

HRID 1636882 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[S:6][C:7]([C:18]([O:20]CC2C=CC=CC=2)=[O:19])=[C:8]([CH3:17])[C:9]=1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:3]>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH3:16][C:13]([O:12][C:10]([C:9]1[C:8]([CH3:17])=[C:7]([C:18]([OH:20])=[O:19])[S:6][C:5]=1[NH:4][C:2]([CH3:1])=[O:3])=[O:11])([CH3:14])[CH3:15]

Participants

4

Reactant 1

HCID 54266376HCID 54266376, compound

Product 1

HCID 54425267HCID 54425267, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound prepared in Example 10 (1.10 g, 2.84 mmol) in EtOAc (225 ml) was added Pd(OH)2 (0.50 g, 0.47 mmol). The flask was then flushed with H2. After 1 day, the reaction was purged with N2 and filtered. The catalyst was washed with hot EtOH (2×). The combined filtrates were concentrated under reduced pressure; to yield 810 mg of a tan solid (95%). 1H-NMR (CDCl3) 1.60 (s, 9H), 2.30 (s, 3H), 2.74 (s, 3H), 5.29 (s, 2H), 7.30-7.50 (m, 5H). 1.56 (s, 9H), 2.25 (s, 3H), 2.67 (s, 3H), 5.60 (brs, 2H) 11.40 (brs, 1H).

Workup

  1. customThe flask was then flushed with H2
  2. customthe reaction was purged with N2
  3. filtrationfiltered
  4. washThe catalyst was washed with hot EtOH (2×)
  5. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-c01fa4a8404a47e0a575eccd3efb6ca9
Source dataset
uspto-grants-2000_03
Patent number
US06037340

Reaction notes

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