Hydrochloric Acid → Methyl p-nitrophenylalanine hydrochloride

HRID 5750

Reaction equation

HRID 5750 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:16]=[CH:15][C:8]([CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH3:17]O>>[ClH:1].[CH3:17][NH:11][C@H:10]([C:12]([OH:14])=[O:13])[CH2:9][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 137064-Nitro-3-phenyl-L-alanine

Product 1

HCID 69555327Methyl p-nitrophenylalanine hydrochloride

Procedure

Dry methanol (200 ml) was saturated with HCl(g) in a two-necked round bottom flask cooled to -10° C. p-Nitrophenylalanine (10.0 g, 47.6 mmol) was added in one portion and left to stir for about 18 hours, the solution was evaporated to near dryness on a rotary evaporator and the precipitated product collected in a Buchner funnel. After drying under vacuum at about 50° C., the yield was 10.97 grams (88.3%). A TLC (thin layer chromatography) of the free amino ester run in CHCl3 :MeOH (4:1) revealed and Rf =0.85-0.88. 1H NMR (220 MHz, D2O, pH 1.5) 8.20 (d,2 J=10.0), 7.53 (d,2,J=10.0), 4.55 (t,1,J=5.00), 3.84 (s,3), 3.43 (m,2); CI-MS 225 ((M+1)/z). Anal. Calcd. for C10H13N2O4Cl: C, 46.07; H, 5.03; N, 10.74; Cl, 13.60. Found: C, 45.87; H, 5.08; N, 10.48; Cl, 13.58.

Workup

  1. additionwas added in one portion
  2. waitleft
  3. customthe solution was evaporated
  4. customon a rotary evaporator
  5. customthe precipitated product collected in a Buchner funnel
  6. customAfter drying under vacuum at about 50° C.

Sources & evidence

ORD record
ord-07d855b37c5b4d328abc877c7bed7d1e
Source dataset
uspto-grants-1993_09
Patent number
US05246692

Linked notes

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