Hydrochloric Acid → 29754-04-9

HRID 2085058Notes

Reaction equation

HRID 2085058 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]([NH2:12])[CH2:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.[ClH:13].[C:14](OCC)(=O)[CH3:15]>C(O)C>[ClH:13].[NH2:12][CH:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[CH2:8][C:9]([O:11][CH2:14][CH3:15])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 69189DL-beta-Phenylalanine

Product 1

HCID 1557106129754-04-9Yield 98.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

DL-3-amino-3-phenylpropionic acid (5.4 g, 0.032 moles) was added to saturated HCl (100 ml) in ethanol. The reaction mixture was stirred for 4 hours at room temperature under nitrogen. HCl in ethanol was removed under vacuum to afford a residue. The concentrated residue was trituated with ethyl acetate. The ethyl acetate was then removed in vacuum and the procedure was repeated twice. The resulting residue was dried under high vacuum to give a yellow solid (7.4 g, 98.6% yield). 1H NMR (400 MHz, CD3OD) δ 7.46-7.41 (m, 5H), 4.70 (m, 1H), 4.16-4.11 (m, 2H), 3.11-2.96 (m, 2H), 1.19 (t, 3H, 7.18 Hz). HRMS (M+H) calculated for C11H15N1O2 194.1176, found 194.1210.

Workup

  1. customwas removed under vacuum
  2. customto afford a residue
  3. customThe ethyl acetate was then removed in vacuum
  4. customThe resulting residue was dried under high vacuum

Sources & evidence

ORD record
ord-40bac3f8a0134008be12651abb37af59
Source dataset
uspto-grants-2004_04
Patent number
US06720315B2

Reaction notes

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