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

HRID 1722896Notes

Reaction equation

HRID 1722896 reaction equation
[ClH:1].[NH2:2][C@@H:3]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH:4]([OH:8])[C:5]([OH:7])=[O:6].[CH:13]1[CH:18]=CC=C[CH:14]=1>C(O)(C)C>[ClH:1].[NH2:2][C@@H:3]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH:4]([OH:8])[C:5]([O:7][CH:13]([CH3:18])[CH3:14])=[O:6]

Participants

5

Reactant 3

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 12879199(2RS,3S)-3-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

Hydrogen chloride was passed into a solution of 4 g of (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoic acid in 50 ml of isopropyl alcohol with stirring under ice-cooling, and 100 ml of dry benzene was added to the mixture. The mixture was heated under reflux for 10 minutes while removing water formed during the reaction using a molecular sieve. The reaction mixture was concentrated under reduced pressure obtain 5.7 g of isopropyl (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoate hydrochloride as a white powder.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 10 minutes
  4. customwhile removing water
  5. customformed during the reaction
  6. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ec2a5e2ca4a242e6a72768ceac8ba919
Source dataset
uspto-grants-1989_08
Patent number
US04857650

Reaction notes

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