3-hydroxy-1,2,3-benzotriazin-4(3H)-one → [4-(3-Pyridyloxymethyl)-2-phenylbenzoyl]alanine methyl ester

HRID 2121166Notes

Reaction equation

HRID 2121166 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]=2)[CH:2]=1.Cl.[CH3:25][O:26][C:27](=[O:31])[C@H:28]([CH3:30])[NH2:29].Cl.CN(C)CCCN=C=NCC.ON1C(=O)C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[CH3:25][O:26][C:27](=[O:31])[C@H:28]([CH3:30])[NH:29][C:13](=[O:14])[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[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 5

HCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733257Alanine methyl ester hydrochlorideHCID 234363704-(3-Pyridyloxymethyl)2-phenylbenzoic acid

Product 1

HCID 69892498[4-(3-Pyridyloxymethyl)-2-phenylbenzoyl]alanine methyl ester

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg (0.33 mmol) of 4-(3-pyridyloxymethyl)-2-phenylbenzoic acid, L-alanine methyl ester hydrochloride (1.5 mmol), 69 mg (0.36 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, and 59 mg (0.36 mmol) of 3-hydroxy1,2,3-benzotriazin-4(3H)-one in 1 mL of N,N-dimethylformamide was added 5 drops of triethylamine. The mixture was stirred at ambient temperature for 24 hours, then poured into 10 mL of 0.6M aqueous sodium bicarbonate and extracted with ethyl acetate (3×5 mL). The combined ethyl acetate layers were back extracted with water (2×5 mL), then brine (1×5 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. The product was purified via chromatography over silica gel, eluting with an appropriate mixture of hexanes and ethyl acetate.

Workup

  1. extractionextracted with ethyl acetate (3×5 mL)
  2. extractionThe combined ethyl acetate layers were back extracted with water (2×5 mL)
  3. dry with materialbrine (1×5 mL), dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified via chromatography over silica gel
  7. washeluting with an appropriate mixture of hexanes and ethyl acetate

Sources & evidence

ORD record
ord-7953df887d344e8089af025376627a64
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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