Water → (R)-3-(4-Methoxybenzyl)-2-oxothiazolidine-4-carboxylic Acid

HRID 2219792

反応式

HRID 2219792 の反応式
[SH:1][CH2:2][CH:3]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:4]([OH:6])=[O:5].[C:17](=O)([O-])[O-:18].[K+].[K+].O.C1N=CN(C(N2C=NC=C2)=O)C=1>C(#N)C>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][N:7]2[C@H:3]([C:4]([OH:6])=[O:5])[CH2:2][S:1][C:17]2=[O:18])=[CH:14][CH:13]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 110210473-Mercapto-2-(4-methoxy-benzylamino)-propionic acid

生成物 1

HCID 11207876(R)-3-(4-Methoxybenzyl)-2-oxothiazolidine-4-carboxylic Acid

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
40 °C

実験手順

A 22 L three-necked round bottom flask fitted with an internal temperature probe and a mechanical stirrer was charged with 3-mercapto-2-(4-methoxybenzylamino)-propionic acid (400.0 g, 1.66 mol), potassium carbonate (480.0 g, 3.47 mol) and 2.80 L of water. The mixture was heated at 40° C. with stirring until it became homogeneous and was then cooled to 20-25° C. A solution of N,N-carbonyldiimidazole (400.0 g, 222.47 mol) in 2.8 L of acetonitrile was added while maintaining an internal reaction temperature of less than 30° C. The reaction was monitored by HPLC and was complete upon the disappearance of starting material. The acetonitrile was removed by distillation at 40° C. and 80-100 torr. Iso-propyl acetate (200 mL) was added and the pH of the mixture was adjusted to 2 with 150 mL of 3M H2SO4. The biphasic mixture was filtered, separated and the organic layer azeotropically dried by distillation at atmospheric pressure. The final measured water content was less than 0.5%. The resulting solution was further diluted with 1.8 L of iso-propyl acetate and used in the next example. 1H NMR (300 MHz, DMSO) δ 7.15 (d, 8.3 Hz, 2H), 6.88 (d, 8.3 Hz, 2H), 4.52 (AB, JAB=15.5 Hz, ΔvAB=238.4 Hz, 2H), 4.31-4.24 (m, 1H), 3.71 (s, 3H), 3.67-3.59 (m, 1H), 3.36-3.28 (m, 1H).

後処理

  1. customA 22 L three-necked round bottom flask fitted with an internal temperature probe and a mechanical stirrer
  2. temperaturewas then cooled to 20-25° C
  3. temperaturewhile maintaining an internal reaction temperature of less than 30° C
  4. customThe acetonitrile was removed by distillation at 40° C.
  5. additionIso-propyl acetate (200 mL) was added
  6. filtrationThe biphasic mixture was filtered
  7. customseparated
  8. customthe organic layer azeotropically dried by distillation at atmospheric pressure
  9. additionThe resulting solution was further diluted with 1.8 L of iso-propyl acetate

出典と根拠

ORDレコード
ord-18e4a78682614b3894f1082fad314314
出典データセット
uspto-grants-2008_08
特許番号
US07414137B2

関連ノート

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