1,4-Dioxane hydrochloride → Methyl 3-amino-3-(naphthalen-2-yl)propanoate hydrochloride

HRID 378135Notes

Reaction equation

HRID 378135 reaction equation
F[C:2](F)(F)C(O)=O.NN=CNC1C=C(C(NCC([NH:24][CH:25]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)[CH2:26][C:27]([OH:29])=[O:28])=O)=O)C=CC=1.[ClH:40].O1CCOCC1>CO>[ClH:40].[NH2:24][CH:25]([C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1)[CH2:26][C:27]([O:29][CH3:2])=[O:28]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 178514385HCID 178514385, compound

Product 1

HCID 69893349Methyl 3-amino-3-(naphthalen-2-yl)propanoate hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of the product of Step A (2.5 g) in methanol (100 ml) was treated with 4N HCl/dioxane (10 ml). The resulting solution was stirred overnight. The excess solvent was removed under reduced pressure and the semi solid was purified by HPLC (RP--CH3CN/H2O). The solid was dissolved in CH3CN/H2O, treated with 20% aqueous HCl (5 ml) and lyophilized to give methyl β-aminonaphthalene-2-propanoate hydrochloride (1.1 g). MS and 1H-NMR were consistent with the structure.

Workup

  1. customThe excess solvent was removed under reduced pressure
  2. customthe semi solid was purified by HPLC (RP--CH3CN/H2O)
  3. dissolutionThe solid was dissolved in CH3CN/H2O
  4. additiontreated with 20% aqueous HCl (5 ml)

Sources & evidence

ORD record
ord-a7825e81e2a34057bed82c615b635570
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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