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

HRID 47707Notes

Reaction equation

HRID 47707 reaction equation
C([NH:4][C:5]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)(C(OCC)=O)[C:6]([O:8]CC)=[O:7])(=O)C.[ClH:26]>>[ClH:26].[N+:23]([C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][C@@H:5]([C:6]([OH:8])=[O:7])[NH2:4])([O-:25])=[O:24]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 229243Diethyl (acetylamino)(3-nitrobenzyl)malonate

Product 1

HCID 69884754(2S)-2-Amino-3-(3-nitrophenyl)propanoic acid hydrochloride

Conditions

Temperature
100 °C

Procedure

A suspension of 34 g of diethyl 2-(acetylamino)-2-(3-nitrobenzyl)malonate in 510 cm3 of concentrated hydrochloric acid is heated at a temperature in the region of 100° C. for 18 hours: a vigorous evolution of gas takes place and the suspension dissolves when hot. The reaction mixture is then cooled to a temperature in the region of 0° C., after which it is stirred for 1 hour at 0° C. and finally filtered through a sinter funnel. The filter cake is washed with twice 50 cm3 of filtrate and dried in a fume cupboard and then in an oven under vacuum (10 Pa) at a temperature in the region of 60° C. 23.4 g of 3-nitrophenylalanine hydrochloride are obtained in the form of white crystals melting at 222° C.

Workup

  1. dissolutionthe suspension dissolves when hot
  2. temperatureThe reaction mixture is then cooled to a temperature in the region of 0° C.
  3. filtrationfinally filtered through a sinter funnel
  4. washThe filter cake is washed with twice 50 cm3 of filtrate
  5. customdried in a fume cupboard
  6. customin the region of 60° C

Sources & evidence

ORD record
ord-417ec7c912ae449591fed87b6ab6f8ba
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

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