1-[2(R)-[1(R)-(benzyloxycarbamoyl)-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperidine → Trocade

HRID 378588Notes

Reaction equation

HRID 378588 reaction equation
C([O:8][NH:9][C:10]([C@H:12]([C@@H:24]([CH2:33][CH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1)[C:25]([N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26])[CH2:13][N:14]1[C:18](=[O:19])[C:17]([CH3:21])([CH3:20])[N:16]([CH3:22])[C:15]1=[O:23])=[O:11])C1C=CC=CC=1>C(O)C.[Pd]>[CH:34]1([CH2:33][C@H:24]([C@@H:12]([C:10](=[O:11])[NH:9][OH:8])[CH2:13][N:14]2[C:18](=[O:19])[C:17]([CH3:21])([CH3:20])[N:16]([CH3:22])[C:15]2=[O:23])[C:25]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:26])[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

4

Reactant 1

HCID 543913361-[2(R)-[1(R)-(benzyloxycarbamoyl)-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperidine

Product 1

HCID 9824350TrocadeYield 85.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

For the debenzylation, a suspension of 5.5 g of 1-[2(R)-[1(R)-(benzyloxycarbamoyl)-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperidine VII in 40 ml of ethanol and 1.7 g of Pd/C (5%) was hydrogenated at 22°/1 bar for 4 h. The suspension was filtered, the filtrate was concentrated completely and the residue was crystallized from water, there being obtained 3.9 g (85%) of pure 1-[3-cyclopentyl-2(R)-[1(R)-(hydroxycarbamoyl)-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]propionyl]piperidine I. MS (EI): 436 (40%).

Workup

  1. customwas hydrogenated at 22°
  2. customfor 4 h
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate was concentrated completely
  5. customthe residue was crystallized from water, there

Sources & evidence

ORD record
ord-5c62e3924130474e94de3766fb8c34c9
Source dataset
uspto-grants-2000_02
Patent number
US06031103

Reaction notes

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