Hydrochloric Acid → HCID 86741925, compound

HRID 986363Notes

Reaction equation

HRID 986363 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]1(O)[CH2:21][CH2:20][CH2:19][CH2:18]1>>[ClH:1].[CH:17]1([O:7][C:6](=[O:8])[CH:5]([OH:9])[C@@H:4]([NH2:3])[CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7298CyclopentanolHCID 14014846HCID 14014846, compound

Product 1

HCID 86741925HCID 86741925, compound

Conditions

Temperature
90 °C

Procedure

Hydrogen chloride was passed into a solution of 300 mg of (2RS, 3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid hydrochloride, which was prepared in Reference Example 2, in 5 ml of cyclopentyl alcohol with stirring under ice-cooling, and then the mixture was heated at 90° C. for 5 hours. The reaction mixture was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=15/1 by volume). The eluate was acidified by adding hydrochloric acid, and then evaporated to dryness under reduced pressure to obtain 380 mg of (2RS, 3S)-3-amino-4-cyclohexyl-2hydroxybutyric acid cyclopentyl ester hydrochloride as a white powder.

Workup

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

Sources & evidence

ORD record
ord-1da99f6162584899a4f60dca7bea768d
Source dataset
uspto-grants-1987_12
Patent number
US04711958

Reaction notes

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