1-[1-Tert-butoxycarbonyl-3-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)propylamino]cyclohexanecarboxylic acid benzyl ester → 1-[1-Tert-butoxycarbonyl-3-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)propylamino]cyclohexanecarboxylic acid

HRID 1459894Notes

Reaction equation

HRID 1459894 reaction equation
C([O:8][C:9]([C:11]1([NH:17][CH:18]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:19][CH2:20][N:21]2[C:29](=[O:30])[C:28]3[CH:27]=[C:26]4[CH:31]=[CH:32][CH:33]=[CH:34][C:25]4=[CH:24][C:23]=3[C:22]2=[O:35])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1>C(O)(=O)C.[Pd]>[C:39]([O:38][C:36]([CH:18]([NH:17][C:11]1([C:9]([OH:10])=[O:8])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[CH2:19][CH2:20][N:21]1[C:29](=[O:30])[C:28]2[CH:27]=[C:26]3[CH:31]=[CH:32][CH:33]=[CH:34][C:25]3=[CH:24][C:23]=2[C:22]1=[O:35])=[O:37])([CH3:42])([CH3:40])[CH3:41]

Participants

4

Reactant 1

HCID 700833741-[1-Tert-butoxycarbonyl-3-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)propylamino]cyclohexanecarboxylic acid benzyl ester

Product 1

HCID 700859441-[1-Tert-butoxycarbonyl-3-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)propylamino]cyclohexanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1-[1-tert-Butoxycarbonyl-3-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)propylamino]cyclohexanecarboxylic acid benzyl ester (416 mg, 0.729 mmol) was dissolved in acetic acid (85 mL) and 10% palladium on activated carbon (440 mg) was added. The mixture was hydrogenated under 3 atmospheres pressure at room temperature for 2 hours. The catalyst was removed by passage through a 0.45 m nylon filter and the filtrate was concentrated under vacuum to afford 1-[1 -tert-butoxycarbonyl-3-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)propylamino]cyclohexanecarboxylic acid as a white solid, 308 mg (88%).

Workup

  1. customThe catalyst was removed by passage through a 0.45 m nylon
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-93a3d612a2744f7c90acdf02e3471b56
Source dataset
uspto-grants-1998_12
Patent number
US05854275

Reaction notes

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