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

HRID 1664242

반응식

HRID 1664242 반응식
[SH:1][CH2:2][C@H: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+].C1N=CN(C(N2C=NC=C2)=O)C=1.C(OC(C)C)(=O)C>C(#N)C.O>[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

참가 물질

7

반응물 4

HCID 7915Isopropyl AcetateHCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 13891591(R)-3-Mercapto-2-(4-methoxybenzylamino)propanoic Acid

생성물 1

HCID 11207876(R)-3-(4-Methoxybenzyl)-2-oxothiazolidine-4-carboxylic Acid수율 70%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
40 °C

실험 절차

A 22 L three-necked round bottom flask fitted with an internal temperature probe and a mechanical stirrer was charged with the title compound from Example 2 (400.0 g, 1.66 mol), K2CO3 (480.0 g, 3.47 mol) and water (2.8 L). The mixture was heated at 40° C. while stirring until it became homogeneous and was then cooled to room temperature. A solution of N,N-carbonyldiimidazole (400.0 g, 222.47 mol) in acetonitrile (2.8 L) was added dropwise at a rate that maintained an internal reaction temperature less than 30° C. The reaction was monitored by HPLC and was complete upon the disappearance of the starting material (about 15 minutes). The acetonitrile was removed by heating at 40° C. and 80-100 torr. Isopropyl acetate (200 mL) was added and the pH of the mixture was adjusted to 2 with 3 M H2SO4. The biphasic mixture was filtered, and the organic phase was isolated. Additional isopropyl acetate was added and the solution was dried by azeotropic distillation. The reaction volume was reduced further until a precipitate began to form. The yellow precipitate was isolated by filtration and dried at 50° C. overnight to afford the title compound (310 g, 70%).

후처리

  1. customA 22 L three-necked round bottom flask fitted with an internal temperature probe and a mechanical stirrer
  2. temperaturewas then cooled to room temperature
  3. temperaturemaintained an internal reaction temperature less than 30° C
  4. customwas complete upon the disappearance of the starting material (about 15 minutes)
  5. customThe acetonitrile was removed
  6. temperatureby heating at 40° C.
  7. additionIsopropyl acetate (200 mL) was added
  8. filtrationThe biphasic mixture was filtered
  9. customthe organic phase was isolated
  10. customthe solution was dried by azeotropic distillation
  11. customto form
  12. customThe yellow precipitate was isolated by filtration
  13. customdried at 50° C. overnight

출처 및 근거

ORD 기록
ord-da119d2ed2164ca9bfd26d0f71661e6d
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039465B2

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