Water → HCID 178451419, compound

HRID 1846814Notes

Reaction equation

HRID 1846814 reaction equation
[C:1]([O:5][C:6](O[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:23][CH:24]1[CH2:27][CH:26]([C:28]2[NH:32][C:31]3[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=3[N:29]=2)[CH2:25]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.O>CN(C1C=CN=CC=1)C.ClCCl>[CH2:16]([O:23][C@@H:24]1[CH2:25][C@H:26]([C:28]2[N:29]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[N:32]=2)[CH2:27]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1.[CH2:16]([O:23][C@H:24]1[CH2:25][C@H:26]([C:28]2[N:29]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[N:32]=2)[CH2:27]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 674813742-(3-(Benzyloxy)cyclobutyl)-1H-benzo[d]imidazole

Product 2

HCID 178451418HCID 178451418, compoundYield 33%HCID 178451419HCID 178451419, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

DMAP (0.020 g, 0.16 mmol) and di-tert-butyldicarbonate (0.83 g, 3.77 mmol) were added to a suspension of 2-(3-(benzyloxy)cyclobutyl)-1H-benzo[d]imidazole (0.96 g, 3.43 mmol) and triethylamine (1.20 mL, 8.58 mmol) in dichloromethane (15 mL) and the mixture was stirred for 16 h. Water was added, the resulting layers were separated, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil. The oil was purified by silica gel chromatography to give tert-butyl 2-(cis-3-(benzyloxy)cyclobutyl)-1H-benzo[d]imidazole-1-carboxylate (0.43 g, 1.14 mmol, 33% yield) and tert-butyl 2-(trans-3-(benzyloxy)cyclobutyl)-1H-benzo[d]imidazole-1-carboxylate (0.47 g, 1.23 mmol, 36% yield).

Workup

  1. customthe resulting layers were separated
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customThe oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-79b2e34ebfbd4da7b5cd48404d1fa16e
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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