Chloromethyl Methyl Ether → Methyl alpha-amino-alpha-(4-methoxymethoxyphenyl)acetate

HRID 839449

Reaction equation

HRID 839449 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[H][H].[CH3:18][O:19][CH2:20]Cl>O.CN(C)C=O>[NH2:1][CH:2]([C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:18][O:19][CH3:20])=[CH:11][CH:12]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

7

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 4123006p-Hydroxyphenylglycine methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 20324417Methyl alpha-amino-alpha-(4-methoxymethoxyphenyl)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

In this preparation 1.81 g. of methyl α-amino-α-(4-hydroxyphenyl)acetate is dissolved in 10 ml. of dimethylformamide under nitrogen and 0.24 g. of sodium hydride is then added. The solution is stirred at room temperature under nitrogen until hydrogen evolution ceases and then 0.80 g. of chloromethyl methyl ether is added. The resulting mixture is warmed at 60° C for 1 hour and then cooled and diluted with water. The aqueous mixture is extracted with ether and the ether extract is dried and evaporated to afford methyl α-amino-α-(4-methoxymethoxyphenyl)acetate.

Workup

  1. customIn this preparation 1.81 g
  2. temperaturecooled
  3. extractionThe aqueous mixture is extracted with ether
  4. extractionthe ether extract
  5. customis dried
  6. customevaporated

Sources & evidence

ORD record
ord-b59e5b18ad26420caf07f211fcad7334
Source dataset
uspto-grants-1978_06
Patent number
US04094978

Linked notes

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