1,1'-Carbonyldiimidazole → (3R)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamide

HRID 9862Notes

Reaction equation

HRID 9862 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C@H:12]([N:17]2[C:21](=[O:22])[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:27])[CH2:13][C:14](O)=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:41][OH:42]>O1CCCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C@H:12]([N:17]2[C:21](=[O:22])[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:27])[CH2:13][C:14]([NH:41][OH:42])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 69663627HCID 69663627, compound

Product 1

HCID 86590653(3R)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamideYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3R)-3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamide was prepared by the procedure of Example 1 from (3R)-3-(3-ethoxy-4-methoxyphenyl)-3-phthalimidopropanoic acid (14.6 g, 39.5 mmol), carbonyldiimidazole (7.1 g, 43.5 mmol) and hydroxylamine hydrochloride (3.3 g, 47.4 mmol) in tetrahydrofuran (50 mL) to afford (3R)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamide as a white solid (13.9 g, 91% yield): mp, 257.0–259.5° C.; 1H NMR (DMSO-d6) δ 1.31 (t, J=6.9 Hz, 3H, CH3), 3.11 (d, J=7.9 Hz, 2H, CH2), 3.72 (s, 3H, CH3), 3.97 (q, J=6.9 Hz, 2H, CH2), 5.67 (t, J=7.8 Hz, 1H, NCH), 6.90 (br s, 2H, Ar), 7.02 (br s, 1H, Ar), 7.86 (br s, 4H, Ar), 8.79 (br s, 1H, OH), 10.59 (br s, 1H, NH); 13C NMR (DMSO-d6) δ 14.67, 34.22, 50.18, 55.44, 63.71, 111.73, 112.36, 119.65, 123.11, 131.18, 131.21, 134.56, 147.67, 148.53, 165.97, 167.61. Anal Calcd for C20H20N2O6: C, 62.49; H, 5.24; N, 7.29. Found: C, 62.79; H, 5.24; N, 7.23;

Sources & evidence

ORD record
ord-5a37c9d35a6747b4bbf078b66156fb78
Source dataset
uspto-grants-2006_08
Patent number
US07091356B2

Reaction notes

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