HCID 178491615, compound → HCID 178491616, compound

HRID 500076Notes

Reaction equation

HRID 500076 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][C@@H:15]([CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH2:14][CH2:13]2)=[O:10])=[CH:4][C:3]=1[O:23][CH3:24]>C(O)C.[Pt]=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][C@@H:15]([CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:14][CH2:13]2)=[O:10])=[CH:4][C:3]=1[O:23][CH3:24]

Participants

4

Reactant 1

HCID 178491615HCID 178491615, compound

Product 1

HCID 178491616HCID 178491616, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a solution of the compound (315 mg) of Example 47 in ethanol (10 ml) was added platinum oxide (30 mg), and the mixture was hydrogenated at 25° C. The catalyst was removed by filtration from the reaction mixture, and the solvent was evaporated under reduced pressure. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 275 mg of the desired compound.

Workup

  1. customwas hydrogenated at 25° C
  2. customThe catalyst was removed by filtration from the reaction mixture
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)

Sources & evidence

ORD record
ord-d8b5d117de1241a6ab6127e42f031daf
Source dataset
uspto-grants-2010_08
Patent number
US07767854B2

Reaction notes

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