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

HRID 1722182Notes

Reaction equation

HRID 1722182 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.O>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

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 962WaterHCID 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 4.0 g of (2RS, 3S)-3-amino-2-hydroxy-5methylhexanoic acid in 50 ml of isopropyl alcohol with stirring under ice-cooling. To the reaction solution was added 100ml of benzene, and the mixture was heated under reflux for 10 minutes with removal of water as formed during the reaction using a molecular seives. The reaction mixture was evaporated under reduced pressure to 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. customas formed during the reaction
  4. customThe reaction mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0252514c0c7344e5ad6faeaf7f821fe3
Source dataset
uspto-grants-1989_08
Patent number
US04853463

Reaction notes

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