HCID 67070123, compound → HCID 11437857, compound

HRID 1441418Notes

Reaction equation

HRID 1441418 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C@@H:17]3[CH:22]4[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]4)[CH2:18]3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[N:19]12[CH2:20][CH2:21][CH:22]([CH2:23][CH2:24]1)[C@@H:17]([O:16][C:13]1[CH:12]=[CH:11][C:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)=[CH:15][CH:14]=1)[CH2:18]2

Participants

4

Reactant 1

HCID 67070123HCID 67070123, compound

Product 1

HCID 11437857HCID 11437857, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product of Example 16A (580 mg, 1.79 mmol) was treated with Pd/C (Aldrich, wt. 10%, 100 mg) in ethanol (50 mL) under H2 at ambient temperature for 30 min. After the reaction was complete, the catalyst was removed through a short column of diatomaceous earth. The filtrate was concentrated under reduced pressure to provide the title compound (520 mg, yield, 99%). 1H NMR (300 MHz, CD3OD) δ 1.44-1.58 (m, 1H), 1.63-1.89 (m, 2H), 1.99-2.13 (m, 1H), 2.15-2.23 (m, 1H), 2.72-3.04 (m, 5H), 3.29-3.39 (m, 1H), 4.50-4.58 (m, 1H), 6.77 (dt, J=8.8, 2.5 Hz, 2H), 6.91 (dt, J=8.8, 2.4 Hz, 2H), 7.32 (dt, J=8.5, 2.5 Hz, 2H), 7.43 (dt, J=9.2, 2.8 Hz, 2H) ppm. MS (DCI/NH3) m/z 295 (M+H)+.

Workup

  1. customthe catalyst was removed through a short column of diatomaceous earth
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f509a43740d34311807dde545f97837c
Source dataset
uspto-grants-2010_02
Patent number
US07655657B2

Reaction notes

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