Hydrochloric Acid → HCID 14014852, compound

HRID 986358Notes

Reaction equation

HRID 986358 reaction equation
[ClH:1].Cl.[NH2:3][C@@H:4]([CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH:5]([OH:9])[C:6]([OH:8])=[O:7].[CH:17](O)([CH3:19])[CH3:18]>>[ClH:1].[CH:17]([O:7][C:6](=[O:8])[CH:5]([OH:9])[C@@H:4]([NH2:3])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([CH3:19])[CH3:18]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 14014846HCID 14014846, compound

Product 1

HCID 14014852HCID 14014852, compound

Procedure

Hydrogen chloride was passed into a solution of 100 mg of (2RS, 3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid hydrochloride in 12 ml of isopropyl alcohol with stirring under ice-cooling, and the mixture was heated under reflux for 2 hours. The reaction mixture was evaporated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol =15/1 by volume), and the eluate was acidified by adding hydrochloric acid. The mixture was evaporated to dryness under reduced pressure to obtain 108 mg of (2RS, 3S)-3-amino-4-cyclohexyl-2hydroxybutyric acid isopropyl ester hydrochloride as a white powder.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customThe reaction mixture was evaporated to dryness under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol =15/1 by volume)
  6. additionby adding hydrochloric acid
  7. customThe mixture was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e282264ed9cc439b93bfc51b60727f0a
Source dataset
uspto-grants-1987_12
Patent number
US04711958

Reaction notes

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