Ammonia → HCID 58653681, compound

HRID 1676079Notes

Reaction equation

HRID 1676079 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]2[N:8]([C@@H:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[N:10][C:6]=2[CH:5]=1)([O-])=O.N.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCOCC1.O.[Cl-].[Na+].O>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]2[N:8]([C@@H:11]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[N:10][C:6]=2[CH:5]=1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 24489Sodium DithioniteHCID 58653691HCID 58653691, compound

Product 1

HCID 58653681HCID 58653681, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of the crude mixture of methyl (3R)-3-(5-nitro-1H-benzimidazol-1-yl)-3-phenylpropanoate and the corresponding 2-ethoxyethanol ester (714 mg, ca. 2.2 mmol) in a mixture of 1,4-dioxane (10 mL) and water (10 mL) was added concentrated ammonia solution (0.3 mL) and sodium dithionite (3.06 g, 17.6 mmol). The solution was stirred at room temperature for 3 hours, then diluted with brine, and extracted with ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, gradient eluting with a mixture of dichloromethane and methanol (95:5, then 9:1), to afford a mixture of the title compound and the corresponding 2-ethoxyethanol ester, which was used directly without any additional purification. [LCMS (Method C, Mobile Phase I) RT=1.95 mins, MH+ 296 (Me-ester) and RT=2.13 mins, MH+ 354 (EtOCH2CH2-ester)].

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined ethyl acetate extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washgradient eluting with a mixture of dichloromethane and methanol (95:5
  7. custom9:1), to afford

Sources & evidence

ORD record
ord-f90f0e84e5304d40afe32a62989d6d32
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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