HCID 57312667, compound → HCID 57249663, compound

HRID 2253701Notes

Reaction equation

HRID 2253701 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[C@@H:7]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)#[N:2]>C(O)(=O)C.C(O)C.[Pt]>[NH2:2][CH2:1][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[C@@H:7]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 1

HCID 57312667HCID 57312667, compound

Product 1

HCID 57249663HCID 57249663, compoundYield 83.3%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

The title compound of Example 93 (1.9 g) was dissolved in 10 ml of acetic acid in a bottle. To the system was added 1.9 g of 5% platinum/carbon (60% water), and the mixture was shaken under hydrogen (40 p.s.i.) for 4 hours. The mixture was diluted with ethanol, filtered through diatomaceous earth (Celite (trademark)) and the filtrate was concentrated. Saturated aqueous sodium bicarbonate was added to the residue until the pH of the mixture was ca. 8, and the mixture was extracted with chloroform. The chloroform extracts were dried (sodium sulfate) and concentrated to obtain 1.6 g of the title compound as an oil.

Workup

  1. filtrationfiltered through diatomaceous earth (Celite (trademark))
  2. concentrationthe filtrate was concentrated
  3. additionSaturated aqueous sodium bicarbonate was added to the residue until the pH of the mixture
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe chloroform extracts were dried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c9087236b69b48019fd082f247e8ce97
Source dataset
uspto-grants-1993_08
Patent number
US05232929

Reaction notes

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