HCID 69667668, compound → HCID 10225272, compound

HRID 860043Notes

Reaction equation

HRID 860043 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([N:18]([C@H:20]([C:25]2[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[CH2:21][C:22]([OH:24])=[O:23])[CH3:19])=[O:17])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2>CCO.C(O)(=O)C.O=[Pt]=O>[NH2:1][C:2]1[N:3]=[C:4]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([N:18]([C@H:20]([C:25]2[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[CH2:21][C:22]([OH:24])=[O:23])[CH3:19])=[O:17])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

5

Reactant 1

HCID 69667668HCID 69667668, compound

Product 1

HCID 10225272HCID 10225272, compound

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of the acid 3-5 (150 mg, 0.34 mmol) in EtOH (30 mL) and acetic acid (4 mL) was degassed with argon. PtO2 (25 mg) was added and the mixture placed under an atmosphere of hydrogen gas (balloon) for 16 hours. The mixture was filtered through celite, the solvent removed and the residue purified by reverse phase HPLC (preppak C-18 column; water/acetonitrile/0.1% TFA gradient). After lyophilization, the title compound 3-6 was obtained as a light yellow powder.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent removed
  3. customthe residue purified by reverse phase HPLC (preppak C-18 column; water/acetonitrile/0.1% TFA gradient)

Sources & evidence

ORD record
ord-e34a8e648b1947598d9dce783d3baeea
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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