HCID 53927006, compound → HCID 11731596, compound

HRID 850596Notes

Reaction equation

HRID 850596 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:7][CH2:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1)[CH3:2].[H][H]>[Pt]=O.C(O)C>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:7][CH2:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[CH2:16][CH2:15][CH2:14][NH:13][C:12]=2[N:11]=1)[CH3:2]

Participants

5

Reactant 2

HCID 53927006HCID 53927006, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11731596HCID 11731596, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 2-7 (24.3 g, 65.1 mmol), platinum oxide (4 g) and ethanol (130 mL) was stirred under a balloon of hydrogen gas for 6 h. Following filtration and evaporation, the residue was chromatographed (silica gel, ethyl acetate) to give 2-8 as a yellow oil. TLC Rf =0.35 (silica, 70:25:5 chloroform/ethyl acetate/methanol) 1H NMR (300 MHz, CDCl3) δ 7.05 (d, 1H, J=6 Hz), 6.37 (m, 1H), 4.74 (brs, 1H), 4.18 (q, 2H, J=7 Hz), 3.9 (2s, 2H), 3.32 (m, 4H), 2.63 (m, 2H), 2.51 (m, 2H), 2.72 (m, 4H), 1.43 (m, 9H), 1.26 (m, 3H).

Workup

  1. filtrationfiltration and evaporation
  2. customthe residue was chromatographed (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-6764f044d74b4ea2960edb4e70308697
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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