Triethylamine → HCID 53892148, compound

HRID 1458415Notes

Reaction equation

HRID 1458415 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[C:8]([OH:15])=[CH:7][C:5]=2[N:6]=1.[CH3:16][C:17]1[NH:18][C:19]2[C:25]([OH:26])=[C:24]([C:27]([O:29][CH3:30])=[O:28])[CH:23]=[CH:22][C:20]=2[N:21]=1.[C:31]([O:35][C:36](O[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:37])([CH3:34])([CH3:33])[CH3:32].C(N(CC)CC)C>C1COCC1>[C:31]([O:35][C:36]([N:6]1[C:5]2[CH:7]=[C:8]([OH:15])[C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:4]=2[N:3]=[C:2]1[CH3:1])=[O:37])([CH3:34])([CH3:33])[CH3:32].[C:42]([O:41][C:39]([N:21]1[C:20]2[CH:22]=[CH:23][C:24]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([OH:26])[C:19]=2[N:18]=[C:17]1[CH3:16])=[O:40])([CH3:43])([CH3:44])[CH3:45]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 22100697HCID 22100697, compoundHCID 178497327HCID 178497327, compound

Product 2

HCID 53892148HCID 53892148, compoundHCID 54327588HCID 54327588, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 2-methyl-6-hydroxy-5-methoxycarbonylbenzimidazole and 2-methyl-4-hydroxy-5-methoxycarbonylbenzimidazole (7.2 g) in THF (50 mL) was added di-tert-butyldicarbonate (7.6 g) and triethylamine (5 mL). After stirring at 50° C. for 6 hours the solvent was removed and the residue was triturated with ethyl acetate and filtered to afford 1-tert-butoxycarbonyl-2-methyl-6-hydroxy-5-methoxycarbonylbenzimidazole and 1-tert-butoxycarbonyl-2-methyl-4-hydroxy-5-methoxycarbonylbenzimidazole.

Workup

  1. customwas removed
  2. customthe residue was triturated with ethyl acetate
  3. filtrationfiltered

Sources & evidence

ORD record
ord-80433fa3809647afba3adb1ed8d38841
Source dataset
uspto-grants-1998_12
Patent number
US05849759

Reaction notes

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