2,3-Dihydro-5-methyl-epsilon-2-dioxo-1H-imidazole-4-hexanoic acid → 6-(5-Methyl-2-oxoimidazolidin-4-yl)hexanoic acid

HRID 247607Notes

Reaction equation

HRID 247607 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:16])[NH:5][C:6]=1[C:7](=O)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[H][H]>C(O)(=O)C.O=[Pt]=O>[CH3:1][CH:2]1[NH:3][C:4](=[O:16])[NH:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 2

HCID 883092,3-Dihydro-5-methyl-epsilon-2-dioxo-1H-imidazole-4-hexanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 6436-(5-Methyl-2-oxoimidazolidin-4-yl)hexanoic acidYield 64%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1.5 g (6.63 mmol) of 4-methyl-5-(5-carboxypentanoyl)-4-imidazolin-2-one in 30 ml of acetic acid was hydrogenated in a Parr shaker apparatus over 0.4 g of PtO2 at 3 atmospheres and ambient temperature for 3 hours until hydrogen uptake ceased. The Pt was removed by filtration and the filtrate concentrated to an oil comprising 1.1 g. The oil was dissolved in water and cooled overnight to afford 0.9 g (64%) of dl-desthiobiotin identical in all respects to authentic material.

Workup

  1. customThe Pt was removed by filtration
  2. concentrationthe filtrate concentrated to an oil
  3. dissolutionThe oil was dissolved in water
  4. temperaturecooled overnight

Sources & evidence

ORD record
ord-f7b88a01f43246abb9949c894140bfe3
Source dataset
uspto-grants-1987_11
Patent number
US04709044

Reaction notes

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