Benzylamine → Methyl 2-(benzylamino)acetate

HRID 396875Notes

Reaction equation

HRID 396875 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 6 b), 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-cb006b976ed0462895fc7e5a484bced8
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

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