Methanol → HCID 21993439, compound

HRID 1977578Notes

Reaction equation

HRID 1977578 reaction equation
[CH2:1]([O:3][C:4]([NH:6][CH:7]([C:13]([OH:15])=[O:14])[CH2:8][CH:9]1[CH2:12][CH2:11][CH2:10]1)=[O:5])[CH3:2].S(Cl)(Cl)=O.[CH3:20]O>>[CH2:1]([O:3][C:4]([NH:6][CH:7]([C:13]([O:15][CH3:20])=[O:14])[CH2:8][CH:9]1[CH2:10][CH2:11][CH2:12]1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 21993433HCID 21993433, compound

Product 1

HCID 21993439HCID 21993439, compound

Conditions

Temperature
-15 °C

Procedure

11 g (51 mmol) of ethoxycarbonyl-3-cyclobutyl-DL-alanine (Example 1, Step A) is dissolved in 100 ml of methanol, cooled to −15° C. and 10 ml (137 mmol) of thionyl chloride is added at constant stirring. Stirring is continued without further cooling. When the reaction mixture reaches room temperature, stirring is continued for further 2 hours. The solution is then evaporated at a pressure of 2.0-2.5 kPa. The residual oil is dissolved in 40 ml of ethyl acetate, washed with 10 ml of 1N HCl, 2×10 ml of 5% NaHCO3 and 2×10 ml of water, dried over anhydrous sodium sulphate and evaporated to dryness at a pressure of 2.0-2.5 kPa. The residue is considered to be pure [yield: 10.8 g (92%), Rf(1)=0.85; Rf(6)=0.65] and is used without further treatment in the next step.

Workup

  1. temperaturewithout further cooling
  2. customreaches room temperature
  3. stirringstirring
  4. customThe solution is then evaporated at a pressure of 2.0-2.5 kPa
  5. dissolutionThe residual oil is dissolved in 40 ml of ethyl acetate
  6. washwashed with 10 ml of 1N HCl, 2×10 ml of 5% NaHCO3 and 2×10 ml of water
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated to dryness at a pressure of 2.0-2.5 kPa

Sources & evidence

ORD record
ord-527e980abb4241f39794b65771c71277
Source dataset
uspto-grants-2001_05
Patent number
US06235707B1

Reaction notes

Loading…