Acetaldehyde → 5-(Benzoxazol-2-yl)-2-methyl-1-tert-butoxycarbonylmethylbenzimidazole

HRID 74274Notes

Reaction equation

HRID 74274 reaction equation
[C:1]([O:5][C:6]([CH2:8][NH:9][C:10]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)=[CH:13][C:11]=1[NH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:26](=O)[CH3:27].OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[C:14]1[CH:15]=[CH:16][C:10]2[N:9]([CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:26]([CH3:27])=[N:12][C:11]=2[CH:13]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674983332-(2-(Tert-butoxycarbonylmethylamino)anilin-5-yl)benzoxazole

Product 1

HCID 674978055-(Benzoxazol-2-yl)-2-methyl-1-tert-butoxycarbonylmethylbenzimidazoleYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-(tert-butoxycarbonylmethylamino)anilin-5-yl)benzoxazole (see Working Example 91-1) (120 mg, 0.353 mmol) in dimethylformamide (2 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 66 μL, 1.06 mmol) and oxone (217 mg, 0.353 mmol), and this was stirred at room temperature for 2 hours. After the reaction was complete, aqueous potassium carbonate solution was added, this was filtered and washed with water. The crystals obtained were purified by silica gel column chromatography to yield the title compound (30.7 mg, 24% yield) as white crystals.

Workup

  1. filtrationthis was filtered
  2. washwashed with water
  3. customThe crystals obtained
  4. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e19a6ef2df6b4adf929f599fe0a11e2c
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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