Triphenylphosphine → methyl N-(4-bromo-5-methylisoxazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate

HRID 1744105Notes

Reaction equation

HRID 1744105 reaction equation
[Br:1][C:2]1[C:3]([NH:8][C:9](=[O:16])[O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[N:4][O:5][C:6]=1[CH3:7].[C:17]([O:25][CH3:26])(=[O:24])[CH:18]([CH2:20][CH:21]([CH3:23])[CH3:22])O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O.CN(C=O)C>[Br:1][C:2]1[C:3]([N:8]([C:9]([O:10][CH2:11][C:12]([Cl:14])([Cl:13])[Cl:15])=[O:16])[C@H:18]([C:17]([O:25][CH3:26])=[O:24])[CH2:20][CH:21]([CH3:23])[CH3:22])=[N:4][O:5][C:6]=1[CH3:7]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 62908Methyl 2-hydroxy-4-methylpentanoateHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 222357552,2,2-Trichloroethyl 4-bromo-5-methylisoxazol-3-ylcarbamate

Product 1

HCID 69152129methyl N-(4-bromo-5-methylisoxazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a dry degassed DMF solution (50 mL) of 2,2,2-trichloroethyl 4-bromo-5-methylisoxazol-3-ylcarbamate (2.67 g, 7.58 mmol), DL methyl leucate (2.31 g, 15.8 mmol), and triphenyl phosphine (4.11 g, 15.7 mmol) was added diisopropyl azodicarboxylate (3.1 ml, 15.7 mmol) at 0° C. over 2 hours. The reaction was allowed to warm to room temperature while stirring overnight. Water was added and the product was extracted with ether (2×) then ethyl acetate (2×), dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (20% ethyl acetate/hexane) to afford methyl N-(4-bromo-5-methylisoxazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate.

Workup

  1. extractionthe product was extracted with ether (2×)
  2. dry with materialethyl acetate (2×), dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f9809eee67b440898bc42faeded0c4f3
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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