Sodium Bicarbonate → HCID 67357185, compound

HRID 577980Notes

Reaction equation

HRID 577980 reaction equation
[CH2:1]([N:8]([CH2:14][CH:15]([OH:17])[CH3:16])[CH2:9][CH:10](O)[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+]>S(=O)(=O)(O)O>[CH2:1]([N:8]1[CH2:14][CH:15]([CH3:16])[O:17][CH:10]([CH2:11][CH3:12])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67358844HCID 67358844, compound2×

Product 1

HCID 67357185HCID 67357185, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-[Benzyl-(2-hydroxy-propyl)-amino]-butan-2-ol (Intermediate 486, 10.5 g, 44.30 mmol) and sulfuric acid (70% w/w, 10 mL) was heated at 150° C. for 36 hour. The reaction mixture was cooled to 0° C., basified with 10% NaHCO3 to pH˜10 and extracted with diethyl ether (3×50 mL). The organic layer was washed with brine (2×25 mL), water (2×25 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography using n-heptane in diethyl ether to give product as a light yellow oil. Yield: 2.0 g (20%)

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionextracted with diethyl ether (3×50 mL)
  3. washThe organic layer was washed with brine (2×25 mL), water (2×25 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography
  8. customto give product as a light yellow oil

Sources & evidence

ORD record
ord-a6eace65b972403f9cd1cd9c3c307067
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

Loading…