112805-65-9 → HCID 86756500, compound

HRID 1531235Notes

Reaction equation

HRID 1531235 reaction equation
[ClH:1].[OH:2][C@@H:3]([CH2:19][NH:20][CH:21]([CH3:23])[CH3:22])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][C:14]([O:16]CC)=[O:15]>Cl.CC(C)=O>[ClH:1].[OH:2][C@@H:3]([CH2:19][NH:20][CH:21]([CH3:23])[CH3:22])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

4

Reactant 1

HCID 9950098112805-65-9

Product 1

HCID 86756500HCID 86756500, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

(S)-Ethyl 3-[2-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]propionate hydrochloride (10 g, 0.029 moles) was dissolved in 6 N hydrochloric acid (200 mL). This solution was refluxed for 16 h and evaporated to dryness to give a white solid. This solid was dissolved in 50 mL of acetone with warming. Trace insoluble solid was removed by filtration through a fluted filter paper and the solution was allowed to cool to room temperature. The white crystalline solid which separated was filtered, washed with ether (2×25 mL) and air dried to give 6.2 g (0.0195 moles, 67.2%) of crude (S)-(−) 3-[2-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]propionic acid hydrochloride, m.p. 123-124° C. The crude acid (7.5 g, 0.023 moles) was dissolved in hot acetone (40 mL) and allowed to cool at room temperature. The white crystalline solid which separated was filtered, washed with ether (50 mL) and recrystallized three times as described above. The product was then dried in vacuo to give 2.5 g (0.00786 moles, 34.1%) of (S)-(−) 3-[2-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]propionic acid hydrochloride as a white crystalline powder; m.p. 125.9° C., Mass spec. (MS/MS) M+1, m/z 282.42.

Workup

  1. temperatureThis solution was refluxed for 16 h
  2. customevaporated to dryness
  3. customto give a white solid
  4. temperaturewith warming
  5. customTrace insoluble solid was removed by filtration through
  6. filtrationa fluted filter paper
  7. customThe white crystalline solid which separated
  8. filtrationwas filtered
  9. washwashed with ether (2×25 mL) and air
  10. customdried

Sources & evidence

ORD record
ord-28e363a36fa040d6aab20fede7999a5c
Source dataset
uspto-grants-2001_03
Patent number
US06197817B1

Reaction notes

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