Acetic Acid → HCID 67103346, compound

HRID 2080814Notes

Reaction equation

HRID 2080814 reaction equation
[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[CH2:5][CH2:6][CH2:7][NH:8][CH2:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)[CH3:2].[C:21]([BH3-])#N.[Na+].C=O.C(O)(=O)C>CO>[CH2:19]([O:18][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][CH2:7][N:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]#[N:15])=[CH:16][CH:17]=1)[CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23155413HCID 23155413, compound

Product 1

HCID 67103346HCID 67103346, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (1.16 g) obtained in Example 44-1 was dissolved in methanol (34.8 ml) and added with sodium cyanoborohydride (1.21 g) and a 36% formaldehyde aqueous solution (0.648 ml). The solution was adjusted to pH 4 with acetic acid and stirred at room temperature for 18 hours. The reaction solution was concentrated under reduced pressure. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (1.22 g) as a yellow oily substance.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-6d41b323407f4ee49e9bc24095f24035
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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