Potassium Iodide → Trityl candesartan cilexetil

HRID 549974

반응식

HRID 549974 반응식
[C:1](=[O:7])([O-:6])[O:2][CH:3](Cl)[CH3:4].[CH3:8][CH2:9][O:10][C:11]1[N:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[C:32]([C:33]4[N:37]([C:38]([C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)([C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)[C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[N:36]=[N:35][N:34]=4)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[C:57]([OH:59])=[O:58])[N:12]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CS(C)=O.O.C1(C)C=CC=CC=1>[CH3:8][CH2:9][O:10][C:11]1[N:19]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[C:32]([C:33]4[N:37]([C:38]([C:45]5[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=5)([C:51]5[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=5)[C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[N:36]=[N:35][N:34]=4)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:25][CH:26]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[C:57]([O:59][CH:3]([O:2][C:1]([O:6][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:7])[CH3:4])=[O:58])[N:12]=1

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 103125632-Ethoxy-1-((2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1H-benzimidazole-7-carboxylic acidHCID 19763757HCID 19763757, 화합물

생성물 1

HCID 11029254Trityl candesartan cilexetil

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
62.5 °C

실험 절차

Carbohexyl 1-chloroethyl carbonate (36 g) is added to a suspension of trityl candesartan (100 g), potassium carbonate (24 g) and potassium iodide (12 g) in DMSO (500 ml) at temperature of 60-65° C. over 30 min. Reaction mass is maintained at 60-65° C. for 2 hrs, added toluene (300 ml) and water (300 ml). Reaction mass is mixed for 15 min., allowed to settle, the layers are separated at 60-65° C. and aqueous layer is extracted with toluene (200 ml). Water (200 ml) washings are given to the combined organic layer and toluene extractions twice at temperature of 60-65° C. Toluene is distilled off from water washed organic layer at temperature below 60° C. under vacuum, ethanol (100 ml) is added, mixed for about 30 min and distilled off solvents under vacuum at temperature below 60° C. under vacuum. Residue is cooled to 30-35° C., ethanol (300 ml) is added, mixed for 2 hrs at 25-30° C. and filtered the product. Wet cake is washed with ethanol (100 ml) and suck dried. Wet weight of Cilexetil trityl candesartan is 180 g

후처리

  1. customReaction mass
  2. customReaction mass
  3. additionis mixed for 15 min.
  4. customthe layers are separated at 60-65° C.
  5. extractionaqueous layer is extracted with toluene (200 ml)
  6. extractionWater (200 ml) washings are given to the combined organic layer and toluene extractions twice at temperature of 60-65° C
  7. distillationToluene is distilled off from water washed organic layer at temperature below 60° C. under vacuum, ethanol (100 ml)
  8. additionis added
  9. additionmixed for about 30 min
  10. distillationdistilled off solvents under vacuum at temperature below 60° C. under vacuum
  11. temperatureResidue is cooled to 30-35° C.
  12. additionethanol (300 ml) is added
  13. additionmixed for 2 hrs at 25-30° C.
  14. filtrationfiltered the product
  15. washWet cake is washed with ethanol (100 ml)
  16. customsuck dried

출처 및 근거

ORD 기록
ord-5bce55e53e2d43d6a86e232036d6f511
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943780B2

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