Dicyclohexylcarbodiimide → N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester

HRID 1739436Notes

Reaction equation

HRID 1739436 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:19])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[NH2:7])[CH3:3].[Br:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][N:29]=1)[C:24](O)=[O:25].O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.C(N(CC)CC)C>[CH2:2]([O:4][C:5](=[O:19])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[NH:7][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][N:29]=[C:21]([Br:20])[CH:22]=1)[CH3:3]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 2227012-Bromoisonicotinic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 186595423,4-dimethoxy-L-phenylalanine ethyl ester-hydrochloride

Product 1

HCID 53678990N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)alanine ethyl esterYield 93.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

3-(3,4-Dimethoxyphenyl)-L-alanine ethyl ester hydrochloride (66 g), triethylamine (33.3 ml), 2-bromoisonicotinic acid (50.6 g), 1-hydroxybenzotriazole monohydrate (38.4 g) and 1,3-dicyclohexylcarbodiimide (51.7 g) are added to methylene chloride (660 ml), and the mixture is stirred at room temperature for four hours. The reaction mixture is washed, dried, and concentrated. The residue is purified by silica gel chromatography (solvent; chloroform:acetone=10:1) to give N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)-L-alanine ethyl ester (93.5 g).

Workup

  1. washThe reaction mixture is washed
  2. customdried
  3. concentrationconcentrated
  4. customThe residue is purified by silica gel chromatography (solvent; chloroform:acetone=10:1)

Sources & evidence

ORD record
ord-4c1f7d599ba24299974f5cebb23668f3
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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