HCID 19969545, compound → HCID 19969562, compound

HRID 974866Notes

Reaction equation

HRID 974866 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[NH:18][C:17](=[O:19])[CH:16]([CH2:20][CH:21]([CH3:23])[CH3:22])[N:15]([O:24]CC2C=CC=CC=2)[C:14]1=[O:32])=[O:12].[H][H]>O1CCOCC1.[C].[Pd]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1([CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[NH:18][C:17](=[O:19])[CH:16]([CH2:20][CH:21]([CH3:23])[CH3:22])[N:15]([OH:24])[C:14]1=[O:32])=[O:12]

Participants

5

Reactant 2

HCID 19969545HCID 19969545, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19969562HCID 19969562, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

0.80 g of 10% palladium-carbon was added to 30 ml of a solution of 1.56 g of (3RS,6SR)-3-(benzothiazol-2-yl)carbamoyl-3-benzyl-1-benzyloxy-6-isobutylpipera- zine-2,5-dione in dioxane. The mixture was stirred at room temperature for 4 hours in a hydrogen current. The reaction mixture was filtered to remove the catalyst. The filtrate was subjected to distillation to remove the solvent. The resulting light brown oily substance was recrystallized using dichloromethane, to obtain 0.56 g of (3RS,6SR)-3-(benzothiazol-2-yl)carbamoyl-3-benzyl-1-hydroxy-6-isobutylpiperazine-2,5-dione.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. distillationThe filtrate was subjected to distillation
  4. customto remove the solvent
  5. customThe resulting light brown oily substance was recrystallized

Sources & evidence

ORD record
ord-22c19ba805ff43ecb77ff6656d24c5c7
Source dataset
uspto-grants-1997_03
Patent number
US05607934

Reaction notes

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