Triphenylphosphine → HCID 69904168, compound

HRID 651079Notes

Reaction equation

HRID 651079 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:8]=[C:9]([CH2:23][N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)[C:10]=1[N:11]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH3:12])=[O:4].[CH2:37](O)[C:38]#[C:39][CH3:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:8]=[C:9]([CH2:23][N:24]2[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]2)[C:10]=1[N:11]([S:13]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:37][C:38]#[C:39][CH3:40])=[CH:20][CH:21]=1)(=[O:15])=[O:14])[CH3:12])=[O:4]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 129912-Butyn-1-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 69905345HCID 69905345, compound

Product 1

HCID 69904168HCID 69904168, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.810 g (1.59 mmol) of the product of Example 73 and 0.594 mL (7.95 mmol) of 2-butyn-1-ol in 8 mL of THF, was added 2.08 g (7.95 mmol) of triphenylphosphine and then 1.25 mL (7.95 mmol) of diethyl azodicarboxylate. The mixture was stirred at room temperature for 18 h, diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed on silica gel with 2% methanol/dichloromethane to provide 0.830 g (93%) of the desired product as a beige solid. Electrospray Mass Spec 562.1 (M+H)+

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel with 2% methanol/dichloromethane

Sources & evidence

ORD record
ord-097f7932e25b42cb9aadb70ce27caf49
Source dataset
uspto-grants-2001_08
Patent number
US06277885B1

Reaction notes

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