Acetic Acid → HCID 68772648, compound

HRID 1398926Notes

Reaction equation

HRID 1398926 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:9]([CH:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[OH:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:27](O)(=O)[CH3:28].[CH:31](=O)[CH3:32].C(O[BH3-])(=O)C.[Na+]>CO>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[CH:11]([OH:12])[C:9]1[N:8]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:7]2[C:2]([N:1]([CH2:27][CH3:28])[CH2:31][CH3:32])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 23670382SodiumacetoxyborohydrideHCID 68773584HCID 68773584, compound

Product 1

HCID 68772648HCID 68772648, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of methyl 3-{7-amino-2-[(2,4-dichlorophenyl)(hydroxy)methyl]-1H-benzimidazol-1-yl}propanoate (6.00 g, 14.7 mmol) and acetic acid (7.4 mL) in methanol (147 mL) was added acetaldehyde (4.95 mL, 88.2 mmol) at 0° C. After 30 min, sodium acetoxyborohydride (18.7 g, 88.2 mmol) was added. After 2 h, the reaction mixture was quenched with water, concentrated in vacuo, diluted with ethyl acetate, washed with aqueous sodium hydroxide (1 M) and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless amorphous (6.30 g, 13.6 mmol, 92%).

Workup

  1. waitAfter 2 h
  2. customthe reaction mixture was quenched with water
  3. concentrationconcentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washwashed with aqueous sodium hydroxide (1 M) and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-a6ee35376a1343e29923510a63ddcdb1
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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