Sodium cyanoborohydride → HCID 67381226, compound

HRID 2409455Notes

Reaction equation

HRID 2409455 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:15]3[NH:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:17])[N:8]([CH2:18][O:19][CH3:20])[C:7]=2[CH:6]=[C:5](/[CH:21]=[N:22]/[N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:4]=1.C([BH3-])#N.[Na+].CO.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[C:16]2[C:15]3[NH:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:17])[N:8]([CH2:18][O:19][CH3:20])[C:7]=2[CH:6]=[C:5]([CH2:21][NH:22][N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[CH:4]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 21893726Hydrochloride methanolHCID 87378600HCID 87378600, compound

Product 1

HCID 67381226HCID 67381226, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (50 mg, 0.12 mmol) prepared in step 2 was dissolved in tetrahydrofuran (2 ml), added with sodium cyanoborohydride (4 mg, 0.06 mmol) and 1.25 N hydrochloric acid methanol solution (5 ml) slowly. The resulting mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure to remove the solvent. The residue was basified with 1 N sodium hydroxide aqueous solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and the solvent was concentrated to dryness. The residue was then purified by flash column chromatography (dichloromethane:methanol=20:1) to obtain the title compound (18 mg, yield: 38%, yellow solid).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the solvent
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationthe solvent was concentrated to dryness
  6. customThe residue was then purified by flash column chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-b481358e12c6469bad9045a8047b3316
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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