Acetic Acid → HCID 3077668, compound

HRID 1461273Notes

Reaction equation

HRID 1461273 reaction equation
[N:1]1([CH2:7][C:8]2[O:12][C:11]([CH2:13][NH:14][CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][NH:19][C:18]3=[C:22]([C:25]#[N:26])[C:23]#[N:24])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C=O.[C:29]([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C>[CH3:29][N:14]([CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][NH:19][C:18]1=[C:22]([C:23]#[N:24])[C:25]#[N:26])[CH2:13][C:11]1[O:12][C:8]([CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 131846HCID 131846, compoundHCID 5003444Sodium cyanoborohydride

Product 1

HCID 3077668HCID 3077668, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 15 ml of acetonitrile were dissolved 904 mg (2.55 mmol) of Compound 28 and 1 ml (12.3 mmol) of 37% aqueous formalin followed by gradual addition of 271 mg (4.30 mmol) of sodium cyanoborohydride at room temperature. The reaction mixture was stirred at room temperature for 30 minutes and, then, adjusted to pH 7.2 with acetic acid. The reaction mixture was further stirred at room temperature for 45 minutes, at the end of which time the solvent was distilled off under reduced pressure. The residue was diluted with 2N sodium hydroxide solution and extracted with methylene chloride. The organic layer was washed with 0.1N sodium hydroxide solution once and, then, extracted with 1N hydrochloric acid twice. The aqueous layer was adjusted to pH 7.8 with 1N sodium hydroxide solution and re-extracted with 4 portions of methylene chloride. The pooled organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. Finally the residue was purified by silica gel column chromatography (chloroform-methanol=10:1) to give 244 mg (26.0%) of Compound 45 as colorless oil.

Workup

  1. stirringThe reaction mixture was further stirred at room temperature for 45 minutes, at the end of which time the solvent
  2. distillationwas distilled off under reduced pressure
  3. additionThe residue was diluted with 2N sodium hydroxide solution
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with 0.1N sodium hydroxide solution once
  6. extractionextracted with 1N hydrochloric acid twice
  7. extractionre-extracted with 4 portions of methylene chloride
  8. dry with materialThe pooled organic layer was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off
  10. customFinally the residue was purified by silica gel column chromatography (chloroform-methanol=10:1)

Sources & evidence

ORD record
ord-872a9330b48848e3af0a949d59c03f37
Source dataset
uspto-grants-1991_12
Patent number
US05075301

Reaction notes

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