Ethanol → 4hydroxy-L-proline ethyl ester hydrochloride

HRID 394417Notes

Reaction equation

HRID 394417 reaction equation
S(Cl)([Cl:3])=O.[OH:5][CH:6]1[CH2:10][NH:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1.[CH2:14](O)[CH3:15]>>[ClH:3].[CH2:14]([O:12][C:11](=[O:13])[C@@H:8]1[CH2:7][CH:6]([OH:5])[CH2:10][NH:9]1)[CH3:15]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 69248L-Proline, 4-hydroxy-, cis-

Product 1

HCID 127093054hydroxy-L-proline ethyl ester hydrochloride

Procedure

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.

Workup

  1. customequipped with an addition funnel
  2. temperatureThe flask was then cooled in a dry ice/acetone bath
  3. customThe funnel was removed
  4. customThe flask was equipped with a reflux condenser and a sodium hydroxide trap
  5. temperaturethe mixture was refluxed for two hours
  6. customThe product was precipitated in ether
  7. customisolated by filtration
  8. washwashed three times with ether
  9. customit was dried under a stream of nitrogen

Sources & evidence

ORD record
ord-3eb8d0f494364333b92057c4088f6fd1
Source dataset
uspto-grants-2003_08
Patent number
US06602497B1

Reaction notes

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