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

HRID 866253ノート

反応式

HRID 866253 の反応式
[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.CN(C=O)C.[Pd]>[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]

参加物

8

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

Ethyl 2-(4-nitro-1H-benzimidazol-1-yl)octanoate (4.44 mmoles, 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 DHF 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 ml 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)

後処理

  1. filtrationThe catalyst was filtered over celite
  2. concentrationThe solution was concentrated
  3. dissolutionThe residue was dissolved in 25 ml DHF
  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

出典と根拠

ORDレコード
ord-3851f5b3a7f3401692f2c38252b38375
出典データセット
uspto-grants-1996_10
特許番号
US05569768

反応ノート

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