diethyl(S)-2-(4-nitrophthalimido)glutarate → diethyl(S)-2-(4-aminophthalimido)glutarate

HRID 381583Notes

Reaction equation

HRID 381583 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([C@@H:13]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8](=[O:9])[C:7]2=[CH:26][CH:27]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([C@@H:13]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8](=[O:9])[C:7]2=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 10429715diethyl(S)-2-(4-nitrophthalimido)glutarate

Product 1

HCID 10043327diethyl(S)-2-(4-aminophthalimido)glutarateYield 88.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of diethyl(S)-2-(4-nitrophthalimido)glutarate (35.6 g, 94.1 mmol) and 10% palladium on carbon (0.5 g) (Aldrich) in ethanol (200 ml) was shaken under a hydrogen atmosphere (40-50 psi) for 26 hours. The solution was filtered through celite and concentrated in vacuo. The residue was purified by chromatography on silica gel (250 g) eluting with diethyl ether:hexane (4:1) to give diethyl(S)-2-(4-aminophthalimido)glutarate as a viscous yellow oil (29.1 g). 1H NMR (DMSO-d6, 300 MHz) δ: 1.10 (t, J=7 Hz, 3H, ester CH3), 1.12 (t, J=7 Hz, 3H, ester CH3), 2.17-2.39 (m, 4H, glu CH2CH2), 3.87-3.98 (m, 2H, ester CH2), 4.05-4.18 (m, 2H, ester CH2), 4.75-4.82 (m, 1H, glu CH), 6.57 (br s, 2H, NH2), 6.82 (dd, J=8,2 Hz, 1H, Ar), 6.93 (d, J=2 Hz, 1H, Ar), 7.51 (d, J=8 Hz, 1H, Ar). Mass spectrum (CI—CH4) 349 (M+1, 40.8%), 303 (60.1%), 275 (100%). Anal. Calculated for C17H20N2O6: C, 58.62; H, 5.79; N, 8.04. Found: C, 58.62; H, 5.80; N, 8.00.

Workup

  1. filtrationThe solution was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel (250 g)
  4. washeluting with diethyl ether:hexane (4:1)

Sources & evidence

ORD record
ord-59a34a8e2d3a4b1cb21ccf5d29a52ca0
Source dataset
uspto-grants-2001_10
Patent number
US06306865B1

Reaction notes

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