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

HRID 431112Notes

Reaction equation

HRID 431112 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) δ1.31 (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) δ14.69, 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-4080be8272ab46c3a28f0ba9845be65f
Source dataset
uspto-grants-2003_12
Patent number
US06656964B2

Reaction notes

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