tert-Butanol → 6-Carboxy-1-(2-Chlorobenzyl)-2-Methylbenzimidazole

HRID 840779Notes

Reaction equation

HRID 840779 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[C:15]([CH3:17])[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[C:13]=2[CH:26]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.C(N(C(C)C)CC)(C)C.[C:53]([OH:57])(C)(C)C>>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[C:15]([CH3:17])[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[C:13]=2[CH:26]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[C:53]([C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[C:15]([CH3:17])[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[C:13]=2[CH:26]=1)([OH:57])=[O:34]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22620337HCID 22620337, compound

Product 2

HCID 186808176-Carboxy-1-(2-Chlorobenzyl)-2-MethylbenzimidazoleHCID 22620337HCID 22620337, compound

Procedure

) 6-t-Butoxycarbonylamino-1-(2-chlorobenzyl)-2-methylbenzimidazole By using the method of example 1, 6-t-butoxycarbonylamino-1-(2-chlorobenzyl)-2-methylbenzimidazole (0.760 g) is obtained from 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole (1.01 g), diphenylphosphorylazide (1 ml), diisopropylethylamine (1 ml), and t-butylalcohol (25 ml). 1H-NMR (CDCl3, δ): 1.49 (9H, s), 2.47 (3H, s), 5.37 (2H, s), 6.41(1H, d, J=7.5 Hz), 6.55 (1H, br s), 6.93 (1H, dd, J=1.9 and 8.6 Hz), 7.08 (1H, t, J=7.5 Hz), 7.22 (1H, t), 7.44(1H, d, J=8.0 Hz), 7.62 (2H, d, J=8.6 Hz).

Sources & evidence

ORD record
ord-b8140557d0344be1a7e47eef4360fc7b
Source dataset
uspto-grants-2002_04
Patent number
US06369092B1

Reaction notes

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