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 2197273Notes

Reaction equation

HRID 2197273 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). % 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-6a81682f06c34492abf257f586af6e1f
Source dataset
uspto-grants-2012_12
Patent number
US08338471B2

Reaction notes

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