Sodium Carbonate → 3-(3-Cyclopentyloxy-4-methoxyphenyl)-3-phthalimidopropanoic acid

HRID 323720ノート

反応式

HRID 323720 の反応式
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].C(OC(N1[C:36](=[O:37])[C:35]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]2[C:33]1=[O:42])=O)C>C(#N)C.O>[CH:16]1([O:15][C:9]2[CH:8]=[C:7]([CH:2]([N:1]3[C:36](=[O:37])[C:35]4=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]4[C:33]3=[O:42])[CH2:3][C:4]([OH:6])=[O:5])[CH:12]=[CH:11][C:10]=2[O:13][CH3:14])[CH2:17][CH2:18][CH2:19][CH2:20]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 154354833-Amino-3-(3-cyclopentyloxy-4-methoxyphenyl)propanoic acid

生成物 1

HCID 98016133-(3-Cyclopentyloxy-4-methoxyphenyl)-3-phthalimidopropanoic acid収率 68%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of 3-amino-3-(3-cyclopentyloxy-4-methoxyphenyl)propanoic acid (3.00 g, 10.8 mmol) and sodium carbonate (1.20 g, 11.3 mmol) in acetonitrile (30 mL) and water (30 mL) under nitrogen was stirred at room temperature for 15 minutes. To the resulting solution was added N-ethoxycarbonyl phthalimide (2.36 g, 10.8 mmol). The resulting mixture was stirred at room temperature for 18 hours. Most of solvent was removed in vacuo. To the solution was added hydrochloric acid (6N) until the pH of solution <1 to give a suspension and stirring was continued for 1 hour. The suspension was filtered, the solid was washed with water (2×10 mL), and then was dried in a vacuum oven overnight (60° C., <1 torr) to afford 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-phthalimidopropanoic acid as a white solid (3.0 g, 68% yield): mp, 168.0-169.0° C.; 1H NMR (DMSO-d6) δ1.55-1.88 (m, 8H, C5H8), 3.27 (dd, J=6.9, 16.5 Hz, 1H, CHH), 3.51 (dd, J=8.9, 16.5 Hz, 1H, CHH), 3.71 (s, 3H, CH3), 4.71-4.75 (m, 1H, CH), 5.61 (dd, J=6.9, 8.8 Hz, 1H, NCH), 6.87-6.95 (m, 2H, Ar), 7.03 (br s, 1H, Ar), 7.81-7.91 (m, 4H, Ar), 12.4 (br s, 1H, OH); 13C NMR (DMSO-d6) δ23.51, 32.14, 32.17, 36.07, 50.08, 55.52, 79.57, 112.15, 113.97, 119.39, 123.17, 131.09, 131.19, 134.66, 146.77, 149.16, 167.67, 171.72; Anal Calcd for C23H23NO6: C, 67.47; H, 5.66; N, 3.42. Found: C, 67.21; H, 5.46; N, 3.45.

後処理

  1. stirringThe resulting mixture was stirred at room temperature for 18 hours
  2. customMost of solvent was removed in vacuo
  3. additionTo the solution was added hydrochloric acid (6N) until the pH of solution <1
  4. customto give a suspension
  5. stirringstirring
  6. waitwas continued for 1 hour
  7. filtrationThe suspension was filtered
  8. washthe solid was washed with water (2×10 mL)
  9. customwas dried in a vacuum oven overnight (60° C., <1 torr)

出典と根拠

ORDレコード
ord-0092cfc95615493f97e6a3113c542326
出典データセット
uspto-grants-2001_04
特許番号
US06214857B1

反応ノート

読み込み中…