Methyl bromoacetate → N-(7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)glycine methyl ester

HRID 5765Notes

Reaction equation

HRID 5765 reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[CH3:14][O:15][C:16](=[O:19])[CH2:17]Br>C(OCC)C>[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 139145927-Methoxy-1,2,3,4-tetrahydronaphthalen-1-amine

Product 1

HCID 19794097N-(7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)glycine methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

367.0 g of 1-amino-7-methoxy-1,2,3,4-tetrahydronaphthalene are solved in 1500 ml of diethyl ether. To this solution is dropwise added a solution of 158.3 g of bromoacetic acid methyl ester in 450 ml of diethyl ether. The mixture is stirred at room temperature for 70 hours. The precipitate is separated and the solution is concentrated to dryness, yielding N-(7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl) glycine methyl ester quantitatively.

Workup

  1. customThe precipitate is separated
  2. concentrationthe solution is concentrated to dryness

Sources & evidence

ORD record
ord-07d878beecdd42a5b96e75782c8b11ad
Source dataset
uspto-grants-1993_09
Patent number
US05246915

Reaction notes

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