HCID 53785241, compound → HCID 19384996, compound

HRID 2399869Notes

Reaction equation

HRID 2399869 reaction equation
[CH3:1][C:2]([CH3:28])([O:4][C:5]([NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH:20]=[CH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:19])=[O:18])=[CH:12][CH:11]=1)=[O:6])[CH3:3]>CO.[OH-].[Pd+2].[OH-]>[CH3:3][C:2]([CH3:28])([O:4][C:5]([NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:19])=[O:18])=[CH:12][CH:11]=1)=[O:6])[CH3:1]

Participants

4

Reactant 1

HCID 53785241HCID 53785241, compound

Product 1

HCID 19384996HCID 19384996, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 204 mg (0.507 mmol) of Boc amine from Example 16 in methanol was stirred over 20% palladium hydroxide under an atmosphere of hydrogen overnight. The reaction mixture was then filtered and concentrated. Purification by flash chromatography (silica gel, 30% ethyl acetate/hexane) gave 168 mg (82%) of the title compound as a white solid: 1H NMR (200 MHz, CDCl3) δ7.39-7.21 (m, 3H), 7.15-7.06 (m, 4H), 6.96 (d, 2H, J=8.1 Hz), 6.25 (s, 1H), 4.49 (br s, 1H), 3.35-3.24 (m, 4H), 3.18-3.05 (m, 2H), 2.72 (t, 2H, J=7.1 Hz), 1.40 (s, 9H).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated
  3. customPurification by flash chromatography (silica gel, 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e02f26f92fa44c58887af16cff5250f5
Source dataset
uspto-grants-1995_09
Patent number
US05451677

Reaction notes

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