Ethyl Acetate → 3-(4-aminophthalimido)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxypropionamide

HRID 9843Notes

Reaction equation

HRID 9843 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=[CH:19][C:20]([N+:23]([O-])=O)=[CH:21][CH:22]=[C:15]2[C:14]1=[O:26])C1C=CC=CC=1.C(OCC)(=O)C>C(OCC)(=O)C.CO.O1CCCC1.[OH-].[OH-].[Pd+2]>[NH2:23][C:20]1[CH:19]=[C:16]2[C:17](=[O:18])[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:14](=[O:26])[C:15]2=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 21988651N-Benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(4-nitrophthalimido)propionamide

Product 1

HCID 98438503-(4-aminophthalimido)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxypropionamideYield 102%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 19895526THF ethyl acetate methanolSolvent

Procedure

A mixture of N-Benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(4-nitrophthalimido)-propionamide (2.3 g, 4.42 mmol) and Pd(OH)2/C (600 mg) in ethyl acetate/methanol/tetrahydrofuran (150 mL each) was shaken under hydrogen. After 24 hours the suspension was filtered through a pad of Celite, and then was washed with methanol (30 mL) and methylene chloride (30 mL). The filtrate was concentrated in vacuo to give an oil. The oil was stirred with ethyl acetate (10 mL) to afford 3-(4-aminophthalimido)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxypropionamide as a yellow solid (1.8 g, 100% yield): mp, 193.0–195.0° C.; 1H NMR (DMSO-d6) δ 1.31 (t, J=6.9 Hz, 3H, CH3), 3.05 (d, J=7.9 Hz, 2H, CH2), 3.71 (s, 3H, CH3), 3.96 (q, J=7.0 Hz, 2H, CH2), 5.57 (t, J=7.9 Hz, 1H, NCH), 6.47 (br s, 2H, NH2), 6.77 (dd, J=2.0, 8.3 Hz, 1H, Ar), 6.83–6.88 (m, 3H, Ar), 6.99 (br s, 1H, Ar), 7.45 (d, J=8.3 Hz, 1H, Ar), 8.78 (br s, 1H, OH), 10.55 (1H, NH); 13C NMR (DMSO-d6) δ 14.69, 34.51, 49.75, 55.45, 63.73, 106.82, 111.74, 112.38, 116.32, 116.73, 119.60, 124.89, 131.85, 134.18, 147.62, 148.42, 155.00, 166.111, 167.70, 168.00; Anal Calcd for C20H21N3O6: C, 60.14; H, 5.30; N, 10.52. -Found: C, 60.00; H, 5.34; N, 10.30.

Workup

  1. filtrationAfter 24 hours the suspension was filtered through a pad of Celite
  2. washwas washed with methanol (30 mL) and methylene chloride (30 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give an oil

Sources & evidence

ORD record
ord-6ecd98bd91e74b1eb0e6b30948b578ae
Source dataset
uspto-grants-2006_08
Patent number
US07091356B2

Reaction notes

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