Acetyl chloride → Isohexane ethyl acetate

HRID 1487292Notes

Reaction equation

HRID 1487292 reaction equation
[C:1](Cl)(=O)C.N([C:14]([O:16][C:17]([CH3:20])(C)C)=[O:15])[C@H:6]([C:11](O)=O)[CH2:7][CH:8]([CH3:10])[CH3:9].O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CO.CN(C=O)C>[CH3:11][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9].[CH3:20][CH2:17][O:16][C:14]([CH3:1])=[O:15]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12373896N-Boc-L-Leucine Hydrate

Product 1

HCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Acetyl chloride (0.18 mL) was added dropwise to a solution of the dibromoalkene 9-2 (81.7 mg, 0.179 mmol) in MeOH (1.62 mL), chilled in an ice bath. The reaction mixture was stirred at RT overnight and then evaporated. Boc-Leu-OH—H2O (50 mg, 0.20 mmol), HATU (75 mg, 0.20 mmol), 1.8 mL DMF, and lastly, DIEA (125 μL, 0.72 mmol) were added. After stirring at RT for 5.5 h the mixture was concentrated in vacuo, and then partitioned between EtOAc and saturated aqueous NaHCO3. The organic phase was washed twice with saturated aqueous NaCl, dried (Na2SO4), and concentrated in vacuo. Flash chromatography (silica, 3/1 isohexane—EtOAc) gave compound 9-3 as a white solid (86.3 mg, 85% yield).

Workup

  1. temperaturechilled in an ice bath
  2. customevaporated
  3. stirringAfter stirring at RT for 5.5 h the mixture
  4. concentrationwas concentrated in vacuo
  5. custompartitioned between EtOAc and saturated aqueous NaHCO3
  6. washThe organic phase was washed twice with saturated aqueous NaCl
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d438795134b947bba571363c2aa1d9c1
Source dataset
uspto-grants-2016_08
Patent number
US09428517B2

Reaction notes

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