Diisopropylethylamine → HCID 71006805, compound

HRID 1023555Notes

Reaction equation

HRID 1023555 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C:9]([CH3:14])([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:46][O:47][C:48]1[CH:49]=[C:50]([O:54][C:55]2[CH:60]=[CH:59][C:58]([NH2:61])=[CH:57][CH:56]=2)[CH:51]=[CH:52][CH:53]=1>CN(C)C=O>[CH3:14][C:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:10])[C:11]([NH:61][C:58]1[CH:57]=[CH:56][C:55]([O:54][C:50]2[CH:51]=[CH:52][CH:53]=[C:48]([O:47][CH3:46])[CH:49]=2)=[CH:60][CH:59]=1)=[O:13]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 8070864-(3-methoxyphenoxy)anilineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

Product 1

HCID 71006805HCID 71006805, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-{[(1,1-dimethylethyl)oxy]carbonyl}-2-methylalanine (1.7 g, 8.36 mmol) in dry N,N-dimethylformamide (35 mL), DIPEA (2.434 mL, 13.94 mmol) and then TBTU (2.80 g, 8.71 mmol) were added and the reaction mixture was stirred for 15 minutes at room temperature. (4-{[3-(methyloxy)phenyl]oxy}phenyl)amine (1.5 g, 6.97 mmol) was then added and the reaction mixture was stirred overnight at the same temperature. The reaction was quenched with brine (100 mL) and extracted with ethyl acetate (twice 150 mL). The organic layer was washed with ice cold brine (3 times 100 mL), dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography (Biotage system, 100 g SNAP column) using as eluent a gradient and cyclohexane/ethyl acetate from 100/0 to 70/30 to afford the title compound as a white solid (1.90 g).

Workup

  1. stirringthe reaction mixture was stirred overnight at the same temperature
  2. customThe reaction was quenched with brine (100 mL)
  3. extractionextracted with ethyl acetate (twice 150 mL)
  4. washThe organic layer was washed with ice cold brine (3 times 100 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica gel chromatography (Biotage system, 100 g SNAP column)

Sources & evidence

ORD record
ord-226ff9981b524f24bf456465ce5f8c84
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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