Hydrochloric Acid → Methyl p-nitrophenylalanine hydrochloride

HRID 621761Notes

Reaction equation

HRID 621761 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 Acid2×HCID 887MethanolHCID 137064-Nitro-3-phenyl-L-alanine

Product 1

HCID 69555327Methyl p-nitrophenylalanine hydrochloride

Procedure

Dry methanol (200 ml) was saturated with HCl by bubbling in a three-necked round bottom flask and cooled to -10° C. p-Nitrophenylalanine (10.0 g, 47.6 mmol) was added in one portion and left to stir for two hours, then resaturated with HCl. The reaction flask was stoppered with a drying tube and left to stir at room temperature for 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 50° C., the yield of 1 was 10.97 grams (88.3%). A TLC of the free amino ester run in CHCl3 :MeOH (4:1) revealed an Rf =0.85-0.88. 1H NMR (220 MHz, D2O, pH 1.5) δ 8.20 (d, 2, J=10.0), 7.53 (d, 2, J=10.0), 4.55 (t, 1, J=11.0), 3.84 (s, 3), 3.43 (m, 2); CI-MS 225 ((M+1)/z).

Workup

  1. customby bubbling in a three-necked round bottom flask
  2. additionwas added in one portion
  3. waitleft
  4. customThe reaction flask was stoppered with a drying tube
  5. waitleft
  6. stirringto stir at room temperature for 18 hours
  7. customThe solution was evaporated
  8. customon a rotary evaporator
  9. customthe precipitated product collected in a Buchner funnel
  10. customAfter drying under vacuum at 50° C.

Sources & evidence

ORD record
ord-ab1077a521f047e68a660693f856639a
Source dataset
uspto-grants-1989_04
Patent number
US04824986

Reaction notes

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