Triphenylphosphine → HCID 69152267, compound

HRID 1744156Notes

Reaction equation

HRID 1744156 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:8](=[O:15])[O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])[S:4][N:3]=1.O[C@H:17]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:18]([O:20][CH3:21])=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CN(C=O)C>[CH3:1][C:2]1[CH:6]=[C:5]([N:7]([C:8]([O:9][CH2:10][C:11]([Cl:12])([Cl:14])[Cl:13])=[O:15])[C@H:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:22][CH:23]([CH3:25])[CH3:24])[S:4][N:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 13893049HCID 13893049, compoundHCID 22236063HCID 22236063, compound

Product 1

HCID 69152267HCID 69152267, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice cold solution of 2,2,2-trichloroethyl 3-methylisothiazol-5-ylcarbamate (20.6 g, 71.1 mmol), methyl (2R)-2-hydroxy-4-methylpentanoate (15.9 g, 109 mmol) and triphenylphosphine (28.9 g, 110 mmol) in DMF (260 mL) was slowly added over 15 min diisopropylazodicarboxylate (21.7 mL, 110 mmol). The resulting brown solution was stirred at room temperature for 30 min and then heated to 60° C. for 18 h. The reaction mixture was allowed to cool to room temperature and it was partitioned between EtOAc and water. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified twice by flash chromatography using EtOAc in hexane to afford methyl N-(3-methylisothiazol-5-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]-L-leucinate as a yellow syrup.

Workup

  1. temperatureheated to 60° C. for 18 h
  2. temperatureto cool to room temperature
  3. customit was partitioned between EtOAc and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified twice by flash chromatography

Sources & evidence

ORD record
ord-303dbbe4d40c4c7888082a85564544df
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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