Propanal → HCID 66941722, compound

HRID 348667Notes

Reaction equation

HRID 348667 reaction equation
N[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C(OC)(OC)OC.C([BH3-])#[N:20].[Na+].C(=O)[CH2:24][CH3:25].CCN=C=N[CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36].Cl.[CH:39]1[CH:40]=[CH:41][C:42]2N(O)N=[N:45][C:43]=2[CH:44]=1.[C:49](C1C=CC(NCN)=CC=1)([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50]>CO.CN(C=O)C>[C:49]([NH:45][CH2:43][C:44]1[CH:39]=[CH:40][CH:41]=[CH:42][C:2]=1[C:3]1([CH2:37][N:35]([CH2:34][CH2:33][CH3:32])[CH2:36][CH2:24][CH3:25])[CH:4]=[CH:5][C:6]([C:7]([NH2:20])=[O:9])=[CH:10][CH2:11]1)([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50]

Participants

10

Reactant 7

HCID 527PropanalHCID 9005Trimethyl orthoformateHCID 655264-(Aminomethyl)Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 57228201HCID 57228201, compound

Product 1

HCID 66941722HCID 66941722, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In methanol (4.5 ml), 4-aminomethylbenzoic acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (300 mg) was dissolved. Then, trimethyl orthoformate (300 μl) and sodium cyanoborohydride (501 mg) were added to the solution, and then the whole was cooled to 0° C. Subsequently, the solution was added with propionaldehyde (357 ml) and then stirred at room temperature for 6 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and then washed with a 1 mol/l sodium hydroxide aqueous solution. After that, chloroform was added. The aqueous layer was neutralized with 1 mol/l hydrochloric acid and extraction with chloroform was then carried out. The solvent was distilled off under reduced pressure and the residue was then dried under vacuum, thereby obtaining a crude product (193.3 mg) as a white viscous solid. Subsequently, the crude product was dissolved in DMF (3.0 ml) and then added with WSCI hydrochloride (236 mg) and HOBt (167 mg), followed by stirring at room temperature for 30 minutes. After that, the solution was added with the compound (183 mg) obtained in Example 71-1 and then stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and then washed with water, a 1 mol/l sodium hydroxide aqueous solution, and saturated saline solution, followed by drying with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (213 mg) as a pale-yellow viscous liquid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  5. additionAfter that, chloroform was added
  6. extractionThe aqueous layer was neutralized with 1 mol/l hydrochloric acid and extraction with chloroform
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was then dried under vacuum
  9. customobtaining a crude product (193.3 mg) as a white viscous solid
  10. stirringby stirring at room temperature for 30 minutes
  11. stirringstirred overnight at room temperature
  12. customAfter completion of the reaction
  13. distillationthe solvent was distilled off under reduced pressure
  14. dissolutionThe residue was dissolved in chloroform
  15. washwashed with water
  16. dry with materialby drying with anhydrous sodium sulfate
  17. filtrationAfter filtration
  18. distillationthe solvent was distilled off under reduced pressure
  19. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-f5bd9f300c8340a393ed4f7d4ff7d02d
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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