Triphenylphosphine → HCID 69151351, compound

HRID 1744097Notes

Reaction equation

HRID 1744097 reaction equation
[Cl:1][C:2]([Cl:14])([Cl:13])[CH2:3][O:4][C:5](=[O:12])[NH:6][C:7]1[S:11][N:10]=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:35]([CH2:40][CH:41]([CH3:43])[CH3:42])[C:36]([O:38][CH3:39])=[O:37].CC(OC(/N=N/C(OC(C)C)=O)=O)C>CN(C)C=O.O>[S:11]1[C:7]([N:6]([C:5]([O:4][CH2:3][C:2]([Cl:1])([Cl:13])[Cl:14])=[O:12])[C@H:35]([C:36]([O:38][CH3:39])=[O:37])[CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:8][CH:9]=[N:10]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 62908Methyl 2-hydroxy-4-methylpentanoateHCID 5363146Diisopropyl azodicarboxylateHCID 131725384HCID 131725384, compound

Product 1

HCID 69151351HCID 69151351, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2,2,2-trichloroethylisothiazol-5-ylcarbamate (253 mg, 0.918 mmol), triphenylphosphine (266 mg, 1.01 mmol) and methyl 2-hydroxy-4-methylpentanoate (151 mg, 1.03 mmol) in N,N-dimethylformamide (2.0 mL) at 0° C. was treated dropwise with diisopropylazodicarboxylate (200 μL, 1.02 mmol) and stirred at rt for 5 h. The mixture was then poured into water and extracted with a 1:1 mixture of ether and ethyl acetate (3×). The combined organics were washed with water and saturated sodium chloride solution, dried (Na2SO4) and concentrated. Flash chromatography of the residue on silica gel eluting with a mixture of ethyl acetate and, hexanes (1:3) gave 260 mg of methyl N-isothiazol-5-yl-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate as a faint-yellow oil.

Workup

  1. extractionextracted with a 1:1 mixture of ether and ethyl acetate (3×)
  2. washThe combined organics were washed with water and saturated sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. additionFlash chromatography of the residue on silica gel eluting with a mixture of ethyl acetate and, hexanes (1:3)

Sources & evidence

ORD record
ord-527c03d17b38499b86166d56884ddf41
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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