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Hydrochloric Acid → (S)-2-Amino-3-cyclohexylpropanoic acid hydrochloride

HRID 2380116
Notes
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Reaction equation

HRID 2380116 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].O.[ClH:16]>[Pt]>[CH2:7]1[CH2:6][CH2:5][CH:4]([CH2:3][C@H:2]([NH2:1])[C:10]([OH:12])=[O:11])[CH2:9][CH2:8]1.[ClH:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6140L-PhenylalanineHCID 178418361HCID 178418361, compound

Product 1

HCID 23381533(S)-2-Amino-3-cyclohexylpropanoic acid hydrochlorideYield 91%

Reagents, catalysts & solvents 1

HCID 23939
Platinum
Catalyst

Procedure

A solution of 10.4 g (61.7 mmoles) of L-phenylalanine in 150 ml of 2N aqueous hydrochloric acid was subjected to a medium pressure catalytic hydrogenation reaction in the presence of 1 g of platinum black using a Paar's apparatus under about 4 atmospheres of hydrogen at room temperature for 24 hours. At the end of this time, the precipitated crystalline substance was dissolved by adding 250 ml of water, and the catalyst was removed by filtration. The filtrate was then concentrated to about 150 ml by evaporation under reduced pressure and allowed to stand overnight. The crystalline substance which deposited was collected by filtration and dried to give 12.8 g (yield 91%) of the title compound as white crystals, melting at 232°-234° C.

Workup

  1. dissolutionAt the end of this time, the precipitated crystalline substance was dissolved
  2. customthe catalyst was removed by filtration
  3. concentrationThe filtrate was then concentrated to about 150 ml by evaporation under reduced pressure
  4. filtrationThe crystalline substance which deposited was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-3b421810ad4a400b9d633cafd45b7f04
Source dataset
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05364844

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes