Acetic Acid → HCID 58424850, compound

HRID 2409410Notes

Reaction equation

HRID 2409410 reaction equation
[CH3:1][N:2]1[C:11]2[C:10]3[CH:12]=[C:13]([O:16][CH:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[CH:14]=[CH:15][C:9]=3[NH:8][C:7](=[O:23])[C:6]=2[CH2:5][CH2:4][CH2:3]1.C=O.[C:26](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CO.ClCCl.C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:11]2[C:10]3[CH:12]=[C:13]([O:16][CH:17]4[CH2:18][CH2:19][N:20]([CH3:26])[CH2:21][CH2:22]4)[CH:14]=[CH:15][C:9]=3[NH:8][C:7](=[O:23])[C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 58424943HCID 58424943, compound

Product 1

HCID 58424850HCID 58424850, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The compound (45 mg, 0.13 mmol) prepared in step 2 of Example 13 was dissolved in methanol (3 ml)/dichloromethane (3 ml), sequentially added with formaldehyde (29 μl, 0.38 mmol), acetic acid (12 μl, 0.22 mmol), and sodium triacetoxyborohydride (108 mg, 0.51 mmol) at room temperature. The resulting mixture was stirred overnight at room temperature and poured into cold 2 N sodium hydroxide aqueous solution. The mixture was extracted with chloroform and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was then by flash column chromatography (chloroform:methanol=5:1) to obtain the title compound (28 mg, yield: 66%, yellow oil).

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88d5cd9b03604b3ea6350dfc2ac2f979
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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