Diisopropylethylamine → HCID 57971724, compound

HRID 548245Notes

Reaction equation

HRID 548245 reaction equation
[CH2:1]([O:5][CH:6]([O:8][NH:9][C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=O)=[O:11])[CH3:7])[CH:2]([CH3:4])[CH3:3].C[Si](C)(C)[O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([O:5][CH:6]([O:8][NH:9][C:10](=[O:11])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][OH:23])=[CH:26][CH:27]=1)=[O:20])[CH3:7])[CH:2]([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 11401321403613-26-3HCID 57971679HCID 57971679, compound

Product 1

HCID 57971724HCID 57971724, compoundYield 529.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-(1-Isobutoxy-ethoxycarbamoyl)-heptanoic acid (5.0 g, 1.72 mmol, 1.0 eq) and 4-trimethylsilanyloxymethyl-phenylamine (3.38 g, 1.72 mmol, 1.0 eq) were stirred together in DMF (140 mL). To the mixture was added PyBroP (10.5 g, 2.25 mmol, 1.3 eq) and DiPEA (3.9 mL, 2.25 mmol, 1.3 eq). The reaction was stirred under a nitrogen atmosphere overnight at room temperature. Ethyl acetate (200 mL) and water (200 mL) were added. The aqueous phase was isolated and re-extracted with ethyl acetate (2×100 mL). The combined organic phases were washed with water (2×50 mL) and brine (50 mL), then dried (MgSO4), filtered and concentrated in vacuo. The crude product was dissolved in the minimum of ethyl acetate and purified by passing through a pad of silica. The product was washed through the silica using ethyl acetate and collected in 100 mL conical flasks until elution ceased by LCMS analysis. Purification gave a yellow oil (3.59 g, 53% yield). LCMS purity 61%, m/z 417 [M++Na]+

Workup

  1. customThe aqueous phase was isolated
  2. extractionre-extracted with ethyl acetate (2×100 mL)
  3. washThe combined organic phases were washed with water (2×50 mL) and brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe crude product was dissolved in the minimum of ethyl acetate
  8. custompurified
  9. washThe product was washed through the silica
  10. customcollected in 100 mL conical flasks until elution
  11. customPurification

Sources & evidence

ORD record
ord-aec80c0f8b76438886fa174bea1827a4
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

Loading…