3-hydroxy-1,2,3-benzotriazin-4(3H)-one → HCID 53886204, compound

HRID 2121145Notes

Reaction equation

HRID 2121145 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH:8]=[C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[C:11]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:10]2)[CH:2]=1.ON1C(=O)C2C=CC=CC=2N=N1.Cl.[CH3:38][O:39][C:40](=[O:47])[C@H:41]([CH2:43][CH2:44][S:45][CH3:46])[NH2:42].Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.O.C(N(CC)CC)C>[CH3:38][O:39][C:40](=[O:47])[C@H:41]([CH2:43][CH2:44][S:45][CH3:46])[NH:42][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][C:9]([CH2:8][O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:10][C:11]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 69892413HCID 69892413, compound

Product 1

HCID 53886204HCID 53886204, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution in DMF (3 mL) of 4-(3-pyridyloxymethylene)-2-phenoxybenzoic acid (321 mg), prepared as in Example 157F, was added 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (345 mg, 1.5 mmol) followed by methionine methyl ester hydrochloride (300 mg, 1.5 mmol), ethyl dimethylaminopropyl carbodiimide hydrochloride (288 mg, 1.5 mmol), and triethylamine (280 mg). The reaction mixture was stirred for 15 hours at ambient temperature. The reaction mixture was diluted with water and extracted with toluene. The toluene solution was washed with, dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography on silica gel (75% ethyl acetate-hexanes) gave [4-(3-pyridyloxymethyl)-2-phenoxybenzoyl]methionine methyl ester (425 mg, 98%).

Workup

  1. extractionextracted with toluene
  2. washThe toluene solution was washed with,
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-980f27c79c14419c9aa242c985b12e58
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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