Ethanol → HCID 15374578, compound

HRID 976002Notes

Reaction equation

HRID 976002 reaction equation
S(=O)(=O)(O)O.[C:6]1([CH:12]2[NH:16][CH:15]([C:17]([OH:19])=[O:18])[CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:20](O)[CH3:21]>>[C:6]1([CH:12]2[NH:16][CH:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][CH2:13]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 409781HCID 409781, compound

Product 1

HCID 15374578HCID 15374578, compound

Conditions

Temperature
80 °C

Procedure

Ethyl (2RS,5SR)-5-phenylprolinate may be obtained as follows: 0.5 cm3 of concentrated sulphuric acid is added dropwise to a solution of 5.5 g of (2RS,5SR)-5-phenylproline in 50 cm3 of ethanol. The reaction mixture is then stirred at a temperature in the vicinity of 80° C. for five hours, then cooled to a temperature in the vicinity of 20° C. and concentrated under reduced pressure. The residue is taken up in 50 cm3 of water, brought to a pH in the vicinity of 9 by a normal aqueous sodium hydroxide solution and extracted with 3 times 100 cm3 of ethyl acetate. The combined organic extracts are washed with 50 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The residue is subjected to chromatography on silica [eluent cyclohexane/ethyl acetate (90/10 by volume)]. The fractions containing the expected product are combined and concentrated under reduced pressure. 2.16 g of ethyl (2RS,5SR)-5-phenylprolinate are thus obtained in the form of an oil, used as it is in subsequent syntheses.

Workup

  1. temperaturecooled to a temperature in the vicinity of 20° C.
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with 3 times 100 cm3 of ethyl acetate
  4. washThe combined organic extracts are washed with 50 cm3 of saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. additionThe fractions containing the expected product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5463591d8ac4deea463136cdbcb6dd9
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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