4-(Bromomethyl)benzonitrile → tert-Butyl (4-cyanobenzyl)glycinate

HRID 2410522Notes

Reaction equation

HRID 2410522 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1)#[N:2].[NH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 151417Glycine tert-butyl ester

Product 1

HCID 18000198tert-Butyl (4-cyanobenzyl)glycinate

Procedure

The title compound was prepared following the general procedure 10, starting from 4-cyanobenzyl bromide and tert-butyl glycinate. It was isolated as a colorless oil. 1H NMR (DMSO-d6, 300 MHz) δ 7.78 (d, J=8.3 Hz, 2H), 7.52 (d, J=8.3 Hz, 2H), 3.79 (s, 2H), 3.19 (s, 2H), 2.60 (br s, 1H), 1.41 (s, 9H). HPLC (Method A) Rt 2.17 min (Purity: 97.2%).

Workup

  1. customIt was isolated as a colorless oil

Sources & evidence

ORD record
ord-caad4cb76fc7498782155b45f750c368
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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