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

HRID 431116Notes

Reaction equation

HRID 431116 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) δ1.39 (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) δ14.70, 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-d6c575196b364ed09112b3864d512c1b
Source dataset
uspto-grants-2003_12
Patent number
US06656964B2

Reaction notes

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