Hydrochloric Acid → 5-(Benzoxazol-2-yl)-2-methyl-1-(2-carboxy-n-propyl)benzimidazole

HRID 74304Notes

Reaction equation

HRID 74304 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:29]=[CH:28][C:13]2[N:14]([CH2:18][CH:19]([C:21]([O:23]C(C)(C)C)=[O:22])[CH3:20])[C:15]([CH3:17])=[N:16][C:12]=2[CH:11]=1.[OH-].[Li+].Cl>C1COCC1.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:29]=[CH:28][C:13]2[N:14]([CH2:18][CH:19]([C:21]([OH:23])=[O:22])[CH3:20])[C:15]([CH3:17])=[N:16][C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 674984575-(Benzoxazol-2-yl)-2-methyl-1-(2-tert-butoxycarbonyl-n-propyl)benzimidazole

Product 1

HCID 680688295-(Benzoxazol-2-yl)-2-methyl-1-(2-carboxy-n-propyl)benzimidazoleYield 86.5%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

5-(Benzoxazol-2-yl)-2-methyl-1-(2-tert-butoxycarbonyl-n-propyl)benzimidazole (see Working Example 121-2) (0.4 g, 1.0 mmol) and THF/water=2:1 (40 mL) were charged, and lithium hydroxide (0.043 g, 1.0 mmol) was added at room temperature, and this was heated and stirred for 5 hours. After being kept cool, the liquid was brought to approximately pH 5 with dilute hydrochloric acid (1 M), the crystals obtained were filtered off and washed with distilled water, and then were dried with heating under reduced pressure to yield the title compound (0.29 g, 83% yield) as white crystals.

Workup

  1. temperaturethis was heated
  2. temperatureAfter being kept cool
  3. customthe crystals obtained
  4. filtrationwere filtered off
  5. washwashed with distilled water
  6. customwere dried
  7. temperaturewith heating under reduced pressure

Sources & evidence

ORD record
ord-f25faacc7fe94f34b39ff0e1f3edce43
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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