Triphenylphosphine → HCID 20581790, compound

HRID 1268175Notes

Reaction equation

HRID 1268175 reaction equation
C(=O)([O-])OCC[CH2:5]/[C:6](/[CH3:16])=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([NH:39][S:40]([CH2:43][CH3:44])(=[O:42])=[O:41])=[CH:35][CH:34]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([O:32][C:33]2[CH:34]=[CH:35][C:36]([N:39]([CH2:5]/[C:6](/[CH3:16])=[CH:7]/[C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=3)[S:40]([CH2:43][CH3:44])(=[O:42])=[O:41])=[CH:37][CH:38]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 18542728HCID 18542728, compoundHCID 86595371HCID 86595371, compound

Product 1

HCID 20581790HCID 20581790, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of [3-(3-cyanophenyl)-2-methyl-2-(E)-propenyl]ethyl carbonate (1.10 g) and N-[4-(1-t-butoxycarbonylpiperidin-4-yloxy)phenyl]ethanesulfonamide (1.15 g) in tetrahydrofuran (9 ml) were added tris(dibenzylideneacetone)palladium chloroform complex (78 mg) and triphenylphosphine (39 mg) and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using dichloromethane/ethyl acetate=12/1 as an eluant to give the desired compound (0.58 g, yield 36%) as a colorless amorphous solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-d98f61132cb946a09b1eb0b6497defa9
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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