Hydrochloric Acid → 4hydroxy-L-proline ethyl ester hydrochloride

HRID 2295334Notes

Reaction equation

HRID 2295334 reaction equation
[OH:1][CH:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[ClH:10].[CH2:11](O)[CH3:12]>>[ClH:10].[OH:1][CH:2]1[CH2:6][NH:5][C@H:4]([C:7]([O:9][CH2:11][CH3:12])=[O:8])[CH2:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 69248L-Proline, 4-hydroxy-, cis-

Product 1

HCID 127093054hydroxy-L-proline ethyl ester hydrochlorideYield 95%

Procedure

A slurry of 100 g (760 mmol) of 4-hydroxy-L-proline in 600 mL of absolute ethanol was treated with dry hydrogen chloride until homogeneous. The solution was heated to the reflux temperature for 2 h. Upon cooling in the refrigerator, the product was obtained as white needles which were filtered, washed well with ether, and dried under reduced pressure to yield 141 g (95%) of (5): mp 153°-153.5° C. (lit. mp-147°-148° C.). 1H NMR (DMSO d6) δ1.25 (t, 3H, J=7 Hz), 4,20 (q, 2H, J=7 Hz). 13C NMR (D2O) 24.1, 47.1, 63.6, 68.7, 73.8, 79.1, 177.5; IR (KBr) 3320, 1735 cm-1.

Workup

  1. temperatureThe solution was heated to the reflux temperature for 2 h
  2. temperatureUpon cooling in the refrigerator
  3. customthe product was obtained as white needles which
  4. filtrationwere filtered
  5. washwashed well with ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-7f981b826ef64c2daf7fddfa91483155
Source dataset
uspto-grants-1984_01
Patent number
US04424312

Reaction notes

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