Hydrogen chloride-ethyl acetate → Methyl 2-amino-3-(4-methoxyphenyl)-3-oxopropanoate

HRID 58869Notes

Reaction equation

HRID 58869 reaction equation
Cl.CCOC(C)=O.C(OC([NH:15][CH:16]([C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[O:22])[C:17]([O:19][CH3:20])=[O:18])=O)(C)(C)C>CCOC(C)=O>[NH2:15][CH:16]([C:21]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)=[O:22])[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 117607815HCID 117607815, compound

Product 1

HCID 13290656Methyl 2-amino-3-(4-methoxyphenyl)-3-oxopropanoateYield 102.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HCl-EtOAc (6N solution, 200 mL) was added to a solution of methyl 2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)-3-oxopropanoate (50.0 g, 155 mmol) in EtOAc (300 mL) at ambient temperature with stirring. The reaction mixture was stirred for 30 min and then concentrated to dryness. The residue was washed with petroleum ether (200 mL×3) and dried to afford methyl 2-amino-3-(4-methoxyphenyl)-3-oxopropanoate (HCl salt, 35.5 g, 88% yield).

Workup

  1. stirringThe reaction mixture was stirred for 30 min
  2. concentrationconcentrated to dryness
  3. washThe residue was washed with petroleum ether (200 mL×3)
  4. customdried

Sources & evidence

ORD record
ord-09fd676fe23e4754a6ded635a383fc7e
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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