HCID 59783546, compound → HCID 58388803, compound

HRID 1946564Notes

Reaction equation

HRID 1946564 reaction equation
[CH:1]1[C:6]2[C:7]([C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=3)=[N:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.C1COCC1.[Pt](=O)=O>[CH:1]1[C:6]2[CH:7]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=3)[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 59783546HCID 59783546, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58388803HCID 58388803, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Title compound 4 was dissolved in ethanol (25 mL) and THF (5 mL). Platinum (IV) oxide (0.075 g, 10% wt) was added. The mixture was stirred at room temperature for 3 h under 1 atmosphere of hydrogen. The catalyst was filtered and the filtrate was concentrated under reduced pressure to one third volume. The precipitate was filtered to afford title compound 5 (510 mg, 67%) as a white solid. LRMS (ESI): (calc) 345.14 (found) 346.3 (MH)+. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.88 (d, J=8.4 Hz, 2H), 7.48 (dd, J=7.5, 1.7 Hz, 1H), 7.39 (d, J=8.0 Hz, 2H), 7.33 (td, J=7.7, 1.8 Hz, 1H), 7.19 (td, J=7.4, 1.2 Hz, 1H), 7.11 (dd, J=8.0, 1.2 Hz, 1H), 6.90-6.83 (m, 3H), 6.77 (dd, J=7.9, 1.4 Hz, 1H), 6.50 (td, J=7.3, 1.6 Hz, 1H), 5.55 (d, J=6.1 Hz, 1H), 4.28 (q, J=7.0 Hz, 2H), 1.28 (t, J=7.0 Hz, 3H).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure to one third volume
  3. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-d2c76ea9d956411d923e5e01095eaa3f
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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