Hydrochloric Acid → Ethyl 2-amino-2-(2,6-dimethoxyphenyl)acetate

HRID 594408Notes

Reaction equation

HRID 594408 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]([NH:17]S(C(C)(C)C)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13].Cl.O1CCOCC1>CO>[NH2:17][CH:11]([C:4]1[C:5]([O:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 69084952Ethyl 2-(2,6-dimethoxyphenyl)-2-(1,1-dimethylethylsulfinamido)-acetate

Product 1

HCID 69084421Ethyl 2-amino-2-(2,6-dimethoxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) solution of ethyl 2-(2,6-dimethoxyphenyl)-2-(1,1-dimethylethylsulfinamido)-acetate (4.215 g; 12.27 mmol) in anh. MeOH (120 ml) was treated dropwise with a solution of 4 M HCl in dioxane (6.30 ml; 25.20 mmol). The resulting heterogeneous mixture was further stirred at 0° C., under nitrogen, for 10 min., and then at rt for 1 h. Concentration to dryness under reduced pressure afforded the chlorhydrate salt of ethyl 2-amino-2-(2,6-dimethoxyphenyl)acetate as a yellow oil. LC-MS (conditions D): tR=0.66 min.; [M+H]+: 240.40 g/mol.

Workup

  1. waitat rt for 1 h
  2. concentrationConcentration to dryness under reduced pressure

Sources & evidence

ORD record
ord-67dec960fe6d410a8796eabdb41c494c
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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