(1-{4-[4-(2-Benzyloxycarbamoyl-ethyl)-phenoxy]-benzyl}-2-morpholin-4-yl-2-oxoethyl)-carbamic acid tert-butyl ester → (1-{4-[4-(2-Hydroxycarbamoyl-ethyl)-phenoxy]-benzyl}-2-morpholin-4-yl-2-oxoethyl)-carbamic acid tert-butyl ester

HRID 748988Notes

Reaction equation

HRID 748988 reaction equation
[C:1]([O:5][C:6](=[O:44])[NH:7][CH:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33](=[O:43])[NH:34][O:35]CC3C=CC=CC=3)=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)[C:9]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:44])[NH:7][CH:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:26]=[CH:27][C:28]([CH2:31][CH2:32][C:33](=[O:43])[NH:34][OH:35])=[CH:29][CH:30]=2)=[CH:20][CH:19]=1)[C:9]([N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 59762810(1-{4-[4-(2-Benzyloxycarbamoyl-ethyl)-phenoxy]-benzyl}-2-morpholin-4-yl-2-oxoethyl)-carbamic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 59762804(1-{4-[4-(2-Hydroxycarbamoyl-ethyl)-phenoxy]-benzyl}-2-morpholin-4-yl-2-oxoethyl)-carbamic acid tert-butyl esterYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on BaSO4 (5%, 0.5 g) was added to a degassed solution of the benzyl hydroxamate 15 (1.6 g) in MeOH (50 mL) and the suspension was treated with hydrogen at atmospheric pressure for 6 h. The suspension was filtered over a Celite® bed and concentrated to yield the desired hydroxamate 16 (1.1 g, 81%). 1H NMR (400 MHz, DMSO-d6): 10.35 (s, 1H), 7.20 (d, J=8.4 Hz, 2H), 7.13-7.17 (m, 3H), 6.85 (d, J=8.4 Hz, 2H), 6.81 (d, J=8.8 Hz, 2H), 4.52 (m, 1H), 3.21-3.49 (m, 8H), 2.69-2.83 (m, 4H), 2.20 (t, J=8.0 Hz, 2H), 1.28 (s, 9H).

Workup

  1. filtrationThe suspension was filtered over a Celite® bed
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-99691e7715ea448ca55da0bf678cc3ee
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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