HCID 53654855, compound → HCID 86758387, compound

HRID 2231073Notes

Reaction equation

HRID 2231073 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][N:8]1[C:14](=[O:15])[CH:13]([N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH2:12][CH2:11][C:10](=[O:27])[N:9]1[CH2:28][CH:29]=[CH2:30])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6](=[O:31])[CH2:7][N:8]1[C:14](=[O:15])[CH:13]([N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH2:12][CH2:11][C:10](=[O:27])[N:9]1[CH2:28][CH2:29][CH3:30])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 53654855HCID 53654855, compound

Product 1

HCID 86758387HCID 86758387, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of [2-allyl-6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3,7-dioxo-[1,2]diazepan-1-yl]-acetic acid tert-butyl ester (5b) (380 mg, 0.89 mmol) and 20% palladium (II) hydroxide on carbon (Pearlman's catalyst) (80 mg) in ethanol (10 mL) was stirred under hydrogen atmosphere for 3 hours. The reaction mixture was filtered through Celite and the filtrate was evaporated in vacuo to give 380 mg (99.5% yield) of the title compound. 1H-NMR (500 MHz, CDCl3) δ 1.05-1.09 (t, 3H), 1.47 (s, 9H), 1.71-1.82 (m, 2H), 2.33-2.46 (m, 1H), 5 2.46-2.53 (m, 1H), 3.00-3.09 (m, 1H), 3.43-3.60 (m, 2H), 3.95-4.00 (d, 1H), 4.10-4.18 (m, 1H), 4.54-4.58 (d, 1H), 5.40-5.45 (m, 1H), 7.70-7.76 (m, 2H), 7.80-7.85 (m, 2H). Analytical HPLC: 13.53 min. LC-MS (ES+): m/e=430 (M+H+).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-27fcb958ad6a40d88a53ec53aceafa83
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

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