Diethyl Ether → 3-(3-aminophthalimido)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxypropionamide

HRID 9847Notes

Reaction equation

HRID 9847 reaction equation
C([O:8][NH:9][C:10](=[O:38])[CH2:11][CH:12]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH2:36][CH3:37])[CH:28]=1)[N:13]1[C:17](=[O:18])[C:16]2=[C:19]([N+:23]([O-])=O)[CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:26])C1C=CC=CC=1.CCOCC>C(OCC)(=O)C.CO.[Pd]>[NH2:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:15]2[C:14]([N:13]([CH:12]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH2:36][CH3:37])[CH:28]=3)[CH2:11][C:10]([NH:9][OH:8])=[O:38])[C:17](=[O:18])[C:16]=12)=[O:26]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 9936461N-benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(3-nitrophthalimido)propionamide

Product 1

HCID 99527533-(3-aminophthalimido)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxypropionamideYield 64.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of N-benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(3-nitrophthalimido)-propionamide (1.32 g, 2.54 mmol) and 10% Pd/C (230 mg) in ethyl acetate/methanol (150 mL each) was shaken under 50–60 psi of H2. After 3 days, the suspension was filtered through a pad of Celite, and the pad washed with methanol (75 mL) and methylene chloride (75 mL). The filtrate was concentrated in vacuo to give an oil. The oil was stirred with ether (20 mL) to afford 3-(3-aminophthalimido)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxypropionamide as a yellow solid (650 mg, 64% yield): mp, 143.0–145.0° C.; 1H NMR (DMSO-d6) δ 1.39 (t, J=6.9 Hz, 3H, CH3), 3.16 (d, J=7.8 Hz, 2H, CH2), 3.79 (s, 3H, CH3), 4.05 (q, J=6.9 Hz, 2H, CH2), 5.68 (t, J=7.8 Hz, 1H, NCH), 6.55 (br s, 2H, NH2), 6.98–7.08 (m, 5H, Ar), 7.47–7.53 (m, 1H, Ar), 8.88 (br s, 1H, OH), 10.66 (1H, NH); 13C NMR (DMSO-d6) δ 14.70, 34.37, 49.65, 55.47, 63.75, 108.64, 110.68, 111.77, 112.39, 119.61, 121.40, 131.69, 132.03, 135.19, 146.48, 147.65, 148.47, 166.14, 167.81, 169.18; Anal Calcd for C20H21N3O6: C, 60.14; H, 5.30; N, 10.52. Found: C, 59.76; H, 5.21; N, 10.30.

Workup

  1. filtrationthe suspension was filtered through a pad of Celite
  2. washthe pad washed with methanol (75 mL) and methylene chloride (75 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give an oil

Sources & evidence

ORD record
ord-76170310ada740d388a17b20754d0916
Source dataset
uspto-grants-2006_08
Patent number
US07091356B2

Reaction notes

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