Dicyclohexylcarbodiimide → 2-[4-[2-(2H-tetrazol-5-yl)benzamido]-1H-benzimidazol-1-yl]octanoic acid

HRID 743884노트

반응식

HRID 743884 반응식
[N+:1]([C:4]1[C:12]2[N:11]=[CH:10][N:9]([CH:13]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:14]([O:16]CC)=[O:15])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[N:25]1[NH:26][N:27]=[N:28][C:29]=1[C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](O)=[O:33].C1(N=C=NC2CCCCC2)CCCCC1.OC1C2N=NNC=2C=CC=1>C(O)C.[Pd].CN(C=O)C>[N:28]1[NH:27][N:26]=[N:25][C:29]=1[C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([NH:1][C:4]1[C:12]2[N:11]=[CH:10][N:9]([CH:13]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:14]([OH:16])=[O:15])[C:8]=2[CH:7]=[CH:6][CH:5]=1)=[O:33]

참가 물질

8

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 5551922-(1H-1,2,3,4-tetrazol-5-yl)benzoic acidHCID 21468887Ethyl 2-(4-nitro-1H-benzimidazol-1-yl)octanoateHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 214689902-[4-[2-(2H-tetrazol-5-yl)benzamido]-1H-benzimidazol-1-yl]octanoic acid수율 9.6%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 6228Dimethylformamide용매

실험 절차

Ethyl 2-(4-nitro-1H-benzimidazol-1-yl)octanoate (4.44 moles, 1.48 g.) was hydrogenated over 0.6 g of 5% Pd/C in 100 ml ethanol. The catalyst was filtered over celite. The solution was concentrated. The residue was dissolved in 25 ml DMF and added to a stirred mixture of 2-(2H-tetrazol-5-yl)benzoic acid (4.21 mmoles, 0.80 g), dicyclohexylcarbodiimide (4.31 mmoles, 0.89 g.), and hydroxybenzotriazole (4.44 mmoles, 0.60 g) in 50 mi DMF. The reaction was stirred for 4 hours. The solid was removed by filtration. The reaction was concentrated. The residue was dissolved in ethyl acetate, and washed with water. The pH was adjusted to 8.0 using 5N NaOH. The aqueous layer was acidified to pH 2.5 using 2N HCL, and then extracted with ethyl acetate. The organic phase was separated, washed with water, dried and concentrated. The product was purified over silica gel eluted with 2% EtOH in ethyl acetate with 1% acetic acid to yield 0.18 g of 2-[4-[2-(2H-tetrazol-5-yl)benzamido]-1H-benzimidazol-1-yl]octanoic acid. (MS)

후처리

  1. filtrationThe catalyst was filtered over celite
  2. concentrationThe solution was concentrated
  3. dissolutionThe residue was dissolved in 25 ml DMF
  4. customThe solid was removed by filtration
  5. concentrationThe reaction was concentrated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with water
  8. extractionextracted with ethyl acetate
  9. customThe organic phase was separated
  10. washwashed with water
  11. customdried
  12. concentrationconcentrated
  13. customThe product was purified over silica gel
  14. washeluted with 2% EtOH in ethyl acetate with 1% acetic acid

출처 및 근거

ORD 기록
ord-130fd970185f4a7bac61444fa19e92e6
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556981

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