Hydrochloric Acid → isopropyl (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoate hydrochloride

HRID 846464Notes

Reaction equation

HRID 846464 reaction equation
[NH2:1][CH:2]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]([OH:7])[C:4]([OH:6])=[O:5].[ClH:12].[C:13]1(C)[CH:18]=CC=C[CH:14]=1>C(O)(C)C>[ClH:12].[NH2:1][C@@H:2]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]([OH:7])[C:4]([O:6][CH:13]([CH3:18])[CH3:14])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 1738443-Amino-2-hydroxy-5-methylhexanoic acid

Product 1

HCID 13913909isopropyl (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoate hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-Amino-2-hydroxy-5-methylhexanoic acid (Example A), 26.5 g (0.164 mol), is dissolved in isopropyl alcohol, treated with hydrochloric acid (anhydrous) for five minutes, treated with toluene (250 ml) and 3A molecular seives and warmed to reflux for 15 minutes. The solution is cooled to room temperature, filtered, and the solvents evaporated in vacuo to give the title compound as an extremely hygroscopic foam, 40 g. The foam is used without further purification.

Workup

  1. temperaturewarmed
  2. temperatureto reflux for 15 minutes
  3. filtrationfiltered
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-387fd8d0b14c4ccfb6451d15c30468f0
Source dataset
uspto-grants-1992_08
Patent number
US05135914

Reaction notes

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