تفاعل #481599

ord-3eb8d0f494364333b92057c4088f6fd1

معادلة التفاعل

O=S(Cl)Cl
thionyl chloride
O=C(O)[C@@H]1CC(O)CN1
4-hydroxyproline
CCO
ethanol
CCOC(=O)[C@@H]1CC(O)CN1.Cl
4hydroxy-L-proline ethyl ester hydrochloride

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىequipped with an addition funnel
  2. 2
    درجة الحرارةThe flask was then cooled in a dry ice/acetone bath
  3. 3
    أخرىThe funnel was removed
  4. 4
    أخرىThe flask was equipped with a reflux condenser and a sodium hydroxide trap
  5. 5
    درجة الحرارةthe mixture was refluxed for two hours
  6. 6
    أخرىThe product was precipitated in ether
  7. 7
    أخرىisolated by filtration
  8. 8
    غسيلwashed three times with ether
  9. 9
    أخرىit was dried under a stream of nitrogen

الإجراء التجريبي

200 mL of absolute ethanol were placed in a 500-mL one-necked round-bottomed flask equipped with an addition funnel. The flask was then cooled in a dry ice/acetone bath, then 17 mL (0.23 mmoles) of thionyl chloride were added from the addition funnel over a 10 minute period. The funnel was removed, and 26.2 g (0.20 mmoles) of 4-hydroxyproline were added in one portion while stirring. The flask was equipped with a reflux condenser and a sodium hydroxide trap, and the mixture was refluxed for two hours. The product was precipitated in ether, isolated by filtration, and washed three times with ether, then it was dried under a stream of nitrogen followed by high vacuum.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US06602497B1uspto-grants-2003_08