HCID 19850152, compound → HCID 21282392, compound

HRID 542541Notes

Reaction equation

HRID 542541 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([N:16]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:9]=1)=[O:4]>C(O)C.[Pt]=O>[F:1][C:2]([F:24])([F:25])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([NH:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 19850152HCID 19850152, compound

Product 1

HCID 21282392HCID 21282392, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

The product from step (a) (11.9 g) and platinum oxide (0.2 g) in ethanol (150 ml) was hydrogenated at room temperature and 3 atmospheres pressure for 18 hrs. The catalyst was filtered and the ethanol evaporated to afford the crude product as a red oil (12 g). This was purified by flash chromatography on silica using petroleum ether/ethyl acetate (3.1) as eluant. Evaporation of the major fraction eluted afforded sub-title compound as white crystals (6.1 g) mp 80°-82°.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered
  3. customthe ethanol evaporated
  4. customto afford the crude product as a red oil (12 g)
  5. customThis was purified by flash chromatography on silica
  6. customEvaporation of the major fraction
  7. washeluted

Sources & evidence

ORD record
ord-bcc940b8732d4c07a82f5d3e7a80abf2
Source dataset
uspto-grants-1987_04
Patent number
US04657929

Reaction notes

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