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

HRID 542372Notes

Reaction equation

HRID 542372 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 4.0 g of (2RS, 3S)-3-amino-2-hydroxy-5-methylhexanoic acid in 50 ml of isopropyl alcohol with stirring under ice-cooling, and then 100 ml of dry benzene was added to the reaction mixture, and the mixture was heated under reflux for 10 minutes while removing water formed during the reaction using a molecular sieve. The reaction mixture was evaporated to dryness 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. temperatureunder reflux for 10 minutes
  4. customwhile removing water
  5. customformed during the reaction
  6. customThe reaction mixture was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-fbb099bf2a3f488d9c01b1ec0839721b
Source dataset
uspto-grants-1987_04
Patent number
US04656269

Reaction notes

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