1,1'-Carbonyldiimidazole → 3-Phthalimido-3-(4-butoxy-3-methoxyphenyl)propionamide

HRID 1421312Notes

Reaction equation

HRID 1421312 reaction equation
[C:1]1(=[O:29])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[C:13]([O:22][CH3:23])[CH:12]=2)[CH2:7][C:8](O)=[O:9])[C:4](=[O:24])[C:3]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:2]12.C(N1C=CN=C1)([N:32]1C=CN=C1)=O>>[C:1]1(=[O:29])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[C:13]([O:22][CH3:23])[CH:12]=2)[CH2:7][C:8]([NH2:32])=[O:9])[C:4](=[O:24])[C:3]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:2]12

Participants

3

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 98870583-Phthalimido-3-(4-butoxy-3-methoxyphenyl)propionic acid

Product 1

HCID 98436863-Phthalimido-3-(4-butoxy-3-methoxyphenyl)propionamide

Procedure

By following the procedure of Example 65 utilizing 3-phthalimido-3-(4-butoxy-3-methoxyphenyl)propionic acid and carbonyldiimidazole, there is obtained 0.742 g (74%) of crude product as a pale yellow powder. The crude product was recrystallized from ethyl acetate (16 mL) to afford 0.517 (52%) of 3-phthalimido-3-(4-butoxy-3-methoxyphenyl)propionamide as fine fluffy white needles: HPLC 99.1%; 1H NMR (DMSO-d6)δ 7.95-7.75 (m, 4H, Ar), 7.54 (br s, 1H, CONH), 7.04 (s, 1H, Ar), 7.0-6.75 (m, 2H), 6.86 (br s, 1H, CONH), 5.67 (t, 1H, J=8 Hz), 3.90 (t, 2H, J=6 Hz), 3.73 (s, 3H), 3.20 (d, 1H, J=8 Hz, CH2CO), 1.8-1.55 (m, 2H) 1.5-1.3 (m, 2H), 0.91 (t, 3H, J=7 Hz); 13C NMR (DMSO-d6)δ 171.2, 167.6, 148.8, 147.7, 134.5, 131.6, 131.2, 123.0, 119.4, 112.8, 111.4, 67.8, 55.5, 50.3, 36.9, 30.7, 18.6, 13.6.

Workup

  1. customthere is obtained 0.742 g (74%) of crude product as a pale yellow powder
  2. customThe crude product was recrystallized from ethyl acetate (16 mL)

Sources & evidence

ORD record
ord-f046d67d49784c95931bb9446df6efec
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

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