HCID 21988661, compound → 3-(3-ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3,4-dimethylphthalimido)propionamide

HRID 9856Notes

Reaction equation

HRID 9856 reaction equation
C([O:8][NH:9][C:10](=[O:37])[CH2:11][CH:12]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH2:35][CH3:36])[CH:27]=1)[N:13]1[C:17](=[O:18])[C:16]2=[C:19]([CH3:24])[C:20]([CH3:23])=[CH:21][CH:22]=[C:15]2[C:14]1=[O:25])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.CO.[OH-].[OH-].[Pd+2]>[CH2:35]([O:34][C:28]1[CH:27]=[C:26]([CH:12]([N:13]2[C:17](=[O:18])[C:16]3=[C:19]([CH3:24])[C:20]([CH3:23])=[CH:21][CH:22]=[C:15]3[C:14]2=[O:25])[CH2:11][C:10]([NH:9][OH:8])=[O:37])[CH:31]=[CH:30][C:29]=1[O:32][CH3:33])[CH3:36]

Participants

6

Reactant 2

HCID 21988661HCID 21988661, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 98878853-(3-ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3,4-dimethylphthalimido)propionamideYield 84%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3,4-dimethylphthalimido)propion-amide was prepared by the procedure of Example 16 N-benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(3,4-dimethylphthalimido)propanamide(0.63 g, 1.25 mmol), Pd(OH)2/C (100 mg) and hydrogen (50 psi) in ethyl acetate and methanol (30 mL each) to afford 3-(3-ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3,4-dimethylphthalimido)propionamide as a white solid (430 mg, 84% yield): mp, 197.0–202.5° C.; 1H NMR (DMSO-d6) δ 1.31 (t, J=7.2 Hz, 3H, CH3), 2.35 (s, 3H, CH3), 2.56 (s, 3H, CH3), 3.09 (d, J=7.9 Hz, 2H, CH2), 3.71 (s, 3H, CH3), 3.97 (q, J=6.9 Hz, 2H, CH2), 5.65 (t, J=7.9 Hz, 1H, NCH), 6.89 (br s, 2H, Ar), 7.00 (br s, 1H, Ar), 7.59 (br s, 2H, Ar), 8.78 (br s, 1H, OH), 10.56 (br s, 1H, NH); 13C NMR (DMSO-d6) δ 13.22, 14.65, 19.33, 34.21, 49.88, 55.43, 63.72, 111.75, 112.40, 119.62, 120.39, 127.76, 129.33, 131.36, 134.71, 136.50, 145.13, 147.62, 148.48, 166.02, 167.32, 168.65; Anal Calcd for C22H24N2O6+0.3 H2O: C, 63.24; H, 5.93; N, 6.70. Found: C, 63.11; H, 5.88; N, 6.67.

Sources & evidence

ORD record
ord-902430e271cd4072b47e7f445e58b689
Source dataset
uspto-grants-2006_08
Patent number
US07091356B2

Reaction notes

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