Acetic Acid → HCID 57419866, compound

HRID 563695Notes

Reaction equation

HRID 563695 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[CH2:14]([NH2:16])[CH3:15].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:14]([NH:16][CH2:4][C:3]1[CH:6]=[C:7]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:8]=[CH:9][C:2]=1[OH:1])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 5003444Sodium cyanoborohydrideHCID 574198652-Hydroxy-5-(methanesulfonyl)benzaldehyde

Product 1

HCID 57419866HCID 57419866, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Hydroxy-5-methanesulfonyl-benzaldehyde (0.200 g, 1.0 mmol), ethylamine (2M in THF; 0.75 mL, 1.5 mmol), and sodium cyanoborohydride (0.095 g, 1.5 mmol) were combined in MeOH (10 mL). 4 Å Molecular sieves were added, followed by acetic acid (0.09 mL, 1.5 mmol), and the reaction was stirred for 1 hour. The mixture was filtered, and H2O (0.5 mL) was added and the solution was concentrated. The residue was partitioned between EtOAc (100 mL) and brine (20 mL), and the mixture was neutralized with 1N aqueous HCl (1 mL) and extracted six times with EtOAc, until minimal product was seen in the aqueous layer by analytical tlc. The combined organic layers were dried, filtered, and concentrated to give the title compound.

Workup

  1. addition4 Å Molecular sieves were added
  2. filtrationThe mixture was filtered
  3. additionH2O (0.5 mL) was added
  4. concentrationthe solution was concentrated
  5. customThe residue was partitioned between EtOAc (100 mL) and brine (20 mL)
  6. extractionextracted six times with EtOAc
  7. customThe combined organic layers were dried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-960e1cc7499d43ef8042f9c94969ad92
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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