N-benzyloxy-2-[4-(4-bromophenoxymethyl)-2,5-dioxo-imidazolidin-1-yl]-3-methylbutyramide → 2-[4-(4-Bromophenoxymethyl)-2,5-dioxo-imidazolidin-1-yl]-N-hydroxy-3-methylbutyramide

HRID 910422Notes

Reaction equation

HRID 910422 reaction equation
C([O:8][NH:9][C:10](=[O:31])[CH:11]([N:15]1[C:19](=[O:20])[CH:18]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=2)[NH:17][C:16]1=[O:30])[CH:12]([CH3:14])[CH3:13])C1C=CC=CC=1>CO.[Pd]>[Br:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH:18]2[C:19](=[O:20])[N:15]([CH:11]([CH:12]([CH3:14])[CH3:13])[C:10]([NH:9][OH:8])=[O:31])[C:16](=[O:30])[NH:17]2)=[CH:28][CH:27]=1

Participants

4

Reactant 1

HCID 76578037N-benzyloxy-2-[4-(4-bromophenoxymethyl)-2,5-dioxo-imidazolidin-1-yl]-3-methylbutyramide2×

Product 1

HCID 765780402-[4-(4-Bromophenoxymethyl)-2,5-dioxo-imidazolidin-1-yl]-N-hydroxy-3-methylbutyramideYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The oil obtained in step i above (22i) (271 mg, 0.571 mmol) and 10% Pd/C (31 mg) were stirred in MeOH (25 mL) at room temperature for 3 h under H2 atmosphere, the mixture was filtered through celite, washed with MeOH for several times and then concentrated. The residue was purified by silica gel column chromatography which gave the title compound as an oil (118 mg, 52% yield).

Workup

  1. filtrationthe mixture was filtered through celite
  2. washwashed with MeOH for several times
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography which

Sources & evidence

ORD record
ord-97b13f5ae0a043dfa57903ad263e38a5
Source dataset
uspto-grants-2011_09
Patent number
US08022092B2

Reaction notes

Loading…