Acetic Acid → HCID 23155476, compound

HRID 2080832Notes

Reaction equation

HRID 2080832 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:8]([CH2:18][CH2:19][CH3:20])[C:9]2[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][C:10]=2[N:11]=1.[C:21]([BH3-])#N.[Na+].[C:25](O)(=O)[CH3:26].[CH:29](=O)[CH2:30][CH3:31]>CO>[CH2:29]([N:1]([CH2:21][CH2:25][CH3:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:8]([CH2:18][CH2:19][CH3:20])[C:9]2[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 23155478HCID 23155478, compound

Product 1

HCID 23155476HCID 23155476, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (26.4 mg) obtained in Example 48-4 was dissolved in methanol (2.0 ml) and added with sodium cyanoborohydride (15.8 mg). After the solution was adjusted to pH 4 with acetic acid, propionaldehyde (0.020 ml) was added thereto and the whole was stirred at room temperature for 20 hours. After the solvent was distilled off, the resultant was neutralized with a saturated aqueous sodium hydrogen carbonate solution and the whole was subjected to extraction with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and dried with anhydrous sodium sulfate. The solvent was distilled off, thereby obtaining the subject compound (29.4 mg) as a colorless oily substance.

Workup

  1. additionwas added
  2. distillationAfter the solvent was distilled off
  3. extractionthe whole was subjected to extraction with chloroform
  4. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-a6fb58f62b5d4c62b325d4028ef8a14c
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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