Triethylamine → 2-(4-Bromo-phenylamino)-3-phenyl-propionic acid tert-butyl ester

HRID 2179936Notes

Reaction equation

HRID 2179936 reaction equation
[C:1]([O:5][C:6](=[O:16])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].[Br:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:16])[CH:7]([NH:8][C:21]1[CH:22]=[CH:23][C:18]([Br:17])=[CH:19][CH:20]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79599(4-Bromophenyl)boronic acidHCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoate

Product 1

HCID 207793162-(4-Bromo-phenylamino)-3-phenyl-propionic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of L-phenylalanine tert-butyl ester (1.47 g, 6.64 mmol), 4-bromophenylboronic acid (2.67 g, 13.28 mmol), triethylamine (1.9 mL, 13.28 mmol) and copper (II) acetate (1.21 g, 6.64 mmol) in dichloromethane (50 mL) was stirred at room temperature for 24 h. The solids were removed by filtration through a pad of silica gel and the desired product was obtained by chromatography eluting with 5% ethyl acetate in hexanes. 1H NMR (CDCl3)7.2 (m, 8 H), 6.48 (d, 2 H), 4.18 (t, 2 H, H-2 and NH), 3.08 (d, 2 H), 1.35 (s, 9 H)

Workup

  1. customThe solids were removed by filtration through a pad of silica gel

Sources & evidence

ORD record
ord-bee9f900717b414599814786dd7e1392
Source dataset
uspto-grants-2005_05
Patent number
US06887877B2

Reaction notes

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