tert-Butanol → HCID 9952790, compound

HRID 840769Notes

Reaction equation

HRID 840769 reaction equation
C([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([CH2:12][CH2:13][CH3:14])[N:9]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:8]=2[CH:23]=1)(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.C([N:44]([CH:47](C)C)CC)(C)C.[C:50]([OH:54])([CH3:53])([CH3:52])[CH3:51]>>[C:50]([O:54][C:47]([NH:44][C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([CH2:12][CH2:13][CH3:14])[N:9]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:8]=2[CH:23]=1)=[O:31])([CH3:53])([CH3:52])[CH3:51]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 186808696-Carboxy-1-(2-chlorobenzyl)-2-n-propylbenzimidazole

Product 1

HCID 9952790HCID 9952790, compound

Procedure

6-Carboxy-1-(2-chlorobenzyl)-2-n-propylbenzimidazole (200 mg) is suspended in t-butyl alcohol (5 ml), then diphenylphosphorylazide (0.19 ml) and diisopropyl-ethylamine (0.21 ml) are added at room temperature. The reaction mixture is refluxed for 4 hours. Then, the solution is separated into layers using ethyl acetate and water. After the organic layer is washed with water and dried, it is concentrated under reduced pressure. The residue is developed and purified using column chromatography with ethyl acetate/hexane (1/10˜1/3), recrystallized in ethyl acetate/hexane and 6-t-butoxycarbonyl-amino-1-(2-chlorobenzyl)-2-n-propylbenzinidazole (165 mg) is obtained. (Colorless crystals) 1H-NMR (CDCl3, δ): 0.98 (3H, t, J=8 Hz), 1.50 (9H, s), 1.86 (2H, sextet, J=8 Hz), 2.72 (2H, t, J=8 Hz), 5.38 (2H, s), 6.40 (1H, dd, J=1, 8 Hz), 6.95 (1H, dd, J=1, 10 Hz), 7.08 (1H, dt, J=1, 8 Hz), 7.24 (1H, dt, J=1, 8 Hz), 7.28 (1H, d, J=1 Hz), 7.45 (1H, dd, J=1, 8 Hz), 7.66 (1H, d, J=10 Hz).

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. customThen, the solution is separated into layers
  3. washAfter the organic layer is washed with water
  4. customdried
  5. concentrationit is concentrated under reduced pressure
  6. custompurified
  7. customrecrystallized in ethyl acetate/hexane
  8. custom6-t-butoxycarbonyl-amino-1-(2-chlorobenzyl)-2-n-propylbenzinidazole (165 mg) is obtained

Sources & evidence

ORD record
ord-97e74450344c47feac5ce41931d470f1
Source dataset
uspto-grants-2002_04
Patent number
US06369092B1

Reaction notes

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