Methanol → 4-Hydroxy-L-proline methyl ester hydrochloride

HRID 1976221Notes

Reaction equation

HRID 1976221 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[CH3:14][O:8][C:7](=[O:9])[C@@H:4]1[CH2:3][C@@H:2]([OH:1])[CH2:6][NH:5]1

Participants

4

Reactant 3

HCID 887MethanolHCID 5810L-HydroxyprolineHCID 24386Thionyl Chloride

Product 1

HCID 114353194-Hydroxy-L-proline methyl ester hydrochlorideYield 98%

Conditions

Temperature
-20 °C

Procedure

A solution prepared by dissolving 13.9 g of trans-4-hydroxy-L-proline in 150 ml of methanol was cooled to −20° C. and then 25 ml of thionyl chloride was dropwise added to the solution. After the completion of the dropwise addition, the resulting mixture was stirred at 40° C. for 30 minutes. The reaction solution was concentrated, followed by addition of ether to the resulting residue, filtration of the crystals thus precipitated, washing the crystals with ether and drying them to give 18.86 g (yield 98.0%) of the title compound.

Workup

  1. customA solution prepared
  2. additionAfter the completion of the dropwise addition
  3. concentrationThe reaction solution was concentrated
  4. additionfollowed by addition of ether to the resulting residue, filtration of the crystals
  5. customthus precipitated
  6. washwashing the crystals with ether
  7. customdrying them

Sources & evidence

ORD record
ord-dc8a1cbc1a994cee9db6d2631d45f054
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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