Acetic Acid → HCID 67103871, compound

HRID 2080784Notes

Reaction equation

HRID 2080784 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+].[C:33](O)(=O)[CH3:34].C(=O)C>CO>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:22][CH2:23][CH3:24])[CH2:25][CH2:26][CH3:27])[CH2:33][CH3:34])=[CH:13][CH:14]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66941782{4-[(4-dipropylamino-butylamino)-methyl]-benzyl}-carbamic Acid t-butyl Ester

Product 1

HCID 67103871HCID 67103871, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (289 mg) obtained in Example 23-4 was dissolved in anhydrous methanol (6.0 ml) and added with sodium cyanoborohydride (92.8 mg), acetic acid (1.00 ml), and acetaldehyde (61.3 μl). The whole was stirred overnight at room temperature under a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off. The resultant was dissolved in chloroform and added with a 1 mol/l sodium hydroxide aqueous solution, followed by stirring for a while. The resultant was subjected to extraction with chloroform, washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off, thereby obtaining the subject compound (311 mg) as a pale-yellow oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe resultant was dissolved in chloroform
  4. additionadded with a 1 mol/l sodium hydroxide aqueous solution
  5. stirringby stirring for a while
  6. extractionThe resultant was subjected to extraction with chloroform
  7. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-c3fc53e2d2da48b8ad478d91dd5c30a4
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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