HCID 59253985, compound → HCID 59253940, compound

HRID 83819Notes

Reaction equation

HRID 83819 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19]CC2C=CC=CC=2)=[CH:8][CH:7]=1>CO.CN(C)C=O.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[CH:8][CH:7]=1

Participants

5

Reactant 1

HCID 59253985HCID 59253985, compound

Product 1

HCID 59253940HCID 59253940, compoundYield 24.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

[4-(6-Benzyloxyhexanoylamino)-phenoxy]-acetic acid methyl ester 57 (24 grms, 62.33 mmol) was dissolved in a mixture of methanol (200 ml) and dimethyl form-amide (50 ml) in a pressure vessel. Palladium on carbon (5%, 15 g) was added and the mixture stirred under an atmosphere of hydrogen (4 kg) for 24 hours. Catalyst was removed by filtration, and the solvents distilled off under vacuum. Crude 58 was purified by column chromatography on silica gel using chloroform as eluant to get pure 58 (4.5 g, 24.4%) as a white powder with an m.p. between 87.5-90.4° C. IH NMR (CDCl3+DMSO-d6) δ 1.40 (m, 4H, CH2), 1.60 (m, 2H, CH2), 2.20 (t, 2H, CH2), 3.40 (t, 2H, CH2), 3.68 (s, 3H, ester), 3.94 (bs, 1H, OH), 4.50 (s, 2H, CH2), 6.68 (d, 2H, Ar), 7.42 (d, 2H, Ar), 9.30 (s, 1H, NH).

Workup

  1. customCatalyst was removed by filtration
  2. distillationthe solvents distilled off under vacuum
  3. customCrude 58 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4203522255bb4f78a144eda818c27c42
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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