Acetic Acid → HCID 68309439, compound

HRID 470715Notes

Reaction equation

HRID 470715 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[CH2:13]([O:20][CH2:21][C:22]1([CH2:30][O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:29][C:24]2([CH2:27][C:26](=O)[CH2:25]2)[CH2:23]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([NH:8][CH:26]1[CH2:27][C:24]2([CH2:29][C:22]([CH2:30][O:31][CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)([CH2:21][O:20][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:23]2)[CH2:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 68309440HCID 68309440, compound

Product 1

HCID 68309439HCID 68309439, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzylamine (1.06 ml, 9.70 mmol) and acetic acid (0.56 ml, 9.70 mmol) were added to a dichloromethane (50 ml) solution of the compound (1.70 g, 4.85 mmol) obtained in Step 3 above, the resulting mixture was stirred for 10 minutes under ice cooling and then sodium cyanoborohydride (610 mg, 9.70 mmol) was added to the reaction mixture. After stirring at room temperature for 24 hours, saturated sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [chloroform:methanol=40:1 (v/v)] to give 1.27 g (60%) of the title compound as an oil.

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography [chloroform:methanol=40:1 (v/v)]

Sources & evidence

ORD record
ord-7e3c26dee2a2444f92157dbd300c0ee6
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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