Diisopropylethylamine → Ethyl 7-((2-((tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoate

HRID 2276695Notes

Reaction equation

HRID 2276695 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58]>CN(C=O)C>[C:57]([O:56][C:55]([NH:54][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=1[NH:47][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])=[O:61])([CH3:60])([CH3:58])[CH3:59]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 118383Ethyl hydrogen heptane-1,7-dioateHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 90388837Ethyl 7-((2-((tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoateYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-ethoxy-7-oxoheptanoic acid (2.0 g, 10.6 mmol) in DMF (50 mL) were added HBTU (4.4 g, 11.6 mmol), DIEA (4.1 g, 31.8 mmol) at room temperature. The resulting mixture was stirred for 10 min, then tert-butyl (2-aminophenyl)carbamate (2.43 g, 11.7 mmol) was added to the reaction solution. The reaction mixture was stirred for 12 h at room temperature. The reaction was quenched with water (200 mL). The resulting mixture was extracted by EtOAc (200 mL×2). The organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure. The resulting solid was purified by column chromatography (elute: EtOAc:PE (petroleum ether)=1:4) to afford the desired compound (3.7 g, yield 92.1%) as a light yellow oil.

Workup

  1. stirringThe reaction mixture was stirred for 12 h at room temperature
  2. customThe reaction was quenched with water (200 mL)
  3. extractionThe resulting mixture was extracted by EtOAc (200 mL×2)
  4. dry with materialdried with anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solid was purified by column chromatography (elute: EtOAc:PE (petroleum ether)=1:4)

Sources & evidence

ORD record
ord-edcee32425e14ac880d5b567523af27b
Source dataset
uspto-grants-2015_09
Patent number
US09133105B2

Reaction notes

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