Benzylamine → Methyl 2-(benzylamino)acetate

HRID 431309Notes

Reaction equation

HRID 431309 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH2:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[CH3:6][O:5][C:3](=[O:4])[CH2:2][NH:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 60984Methyl bromoacetate

Product 1

HCID 422659Methyl 2-(benzylamino)acetateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In scheme 6b), methyl bromoacetate 22 is treated with benzylamine in CH2Cl2 at room temperature for 16 h. The N-benzylglycine methyl ester derivative 23 was obtained in 86% yield. This intermediate can be either acylated with a carboxylic acid derivative and DCC in THF or sulfonated with an appropriate sulfonyl chloride and triethylamine in CH2Cl2 to give derivative 24 or 25 as desired in good to excellent yields.

Sources & evidence

ORD record
ord-1d001a777c704630b06c15590b1019d6
Source dataset
uspto-grants-2003_12
Patent number
US06656965B2

Reaction notes

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