HCID 69667668, compound → HCID 10225272, compound

HRID 2120653Notes

Reaction equation

HRID 2120653 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. Mass spectrum: exact mass calculated for C24H33N4O4 (M+H) is 441.2496; found 441.2493.

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-62e4afa27dbf4704bf136780bf1ce7ff
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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