1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-Butyl (methyl(3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoyl]amino)acetate

HRID 748420Notes

Reaction equation

HRID 748420 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([CH2:18][CH2:19][C:20]([OH:22])=O)[CH:15]=[CH:14][CH:13]=2)=[N:3]1.[C:23]([O:27][C:28](=[O:32])[CH2:29][NH:30][CH3:31])([CH3:26])([CH3:25])[CH3:24].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[CH3:31][N:30]([CH2:29][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:32])[C:20](=[O:22])[CH2:19][CH2:18][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([C:4]2[S:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:2](=[O:1])[N:3]=2)[N:17]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5069406Tert-butyl 2-(methylamino)acetateHCID 99013333-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propionic acid

Product 1

HCID 59750205tert-Butyl (methyl(3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoyl]amino)acetateYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propionic acid (0.35 g, 1.1 mmol) was dissolved in N,N-dimethylformamide (4 ml), and N-methylglycine tert-butyl ester (0.24 g, 1.3 mmol), WSC (0.43 g, 2.2 mmol) and HOBt (0.31 g, 2.3 mmol) were successively added thereto. The reaction mixture was stirred for 20 hrs, concentrated under reduced pressure and combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from ethanol-hexane to give the titled compound (0.33 g, 67%) as white crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-ea24705e8edc4e5eb005f036c3aee5e7
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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