Diethyl Ether → HCID 9845253, compound

HRID 1451853Notes

Reaction equation

HRID 1451853 reaction equation
[C:1]1(=[O:26])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH2:7][C:8]([OH:10])=O)[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]12.[CH2:27]([NH2:32])[CH2:28][CH2:29][CH2:30][CH3:31].CCOCC>C(OCC)(=O)C>[CH2:27]([NH:32][C:8](=[O:10])[CH2:7][CH:6]([N:5]1[C:1](=[O:26])[C:2]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:3]2[C:4]1=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8060PentylamineHCID 103608253-(3,4-Dimethoxyphenyl)-3-phthalimidopropanoic acid

Product 1

HCID 9845253HCID 9845253, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

By following the procedure of Example 46 utilizing 3-phthalimido-3-(3,4'-dimethoxyphenyl)propionic acid and amylamine (1.0 equiv) to afford 2.15 g (84%) of crude product. The crude product was dissolved in 150 mL of ethyl acetate and then 50 mL of ether was added and the mixture stirred for 1 hour. The resulting slurry was filtered and the solid dried in vacuo to afford 1.28 g (50%) yield of 3-phthalimido-3-(3',4'-dimethoxyphenyl)propionic amylamide as a white powder: mp 140.5°-142.1° C.; 1H NMR (DMSO-d6, 250 MHz), d 8.05 (t, 1 H, J=5 Hz), 7.85 (m, 4 H), 7.03 (br s, 1 H), 6.90 (m, 3 H), 5.68 (t, 1 H, J=8 Hz), 3.73 (s, 3 H), 3.71 (s, 3 H), 3.19 (d, 2 H, J=8 Hz), 2.8-3.1 (m, 2 H), 0.9-1.3 (m, 6 H), 0.74 (m, 3 H); 13C NMR (DMSO-d6) δ 168.8, 167.7, 148.5, 148.3, 134.5, 131.5, 131.2, 123.1, 119.5, 111.6, 111.1, 55.4, 50.6, 38.2, 37.4, 28.7, 28.3, 21.7, 13.7; Anal. Calcd. for C24H28N2O5. Theoretical: C, 67.9; H, 6.65; N, 6.60. Found: C, 67.84; H, 6.70; N, 6.57.

Workup

  1. customto afford 2.15 g (84%) of crude product
  2. filtrationThe resulting slurry was filtered
  3. customthe solid dried in vacuo

Sources & evidence

ORD record
ord-7471815692604396a3c618b56fa474e2
Source dataset
uspto-grants-1997_02
Patent number
US05605914

Reaction notes

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