HCID 18542728, compound → HCID 18542622, compound

HRID 1268174Notes

Reaction equation

HRID 1268174 reaction equation
C(=O)([O-])OCC[CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([NH:38][S:39]([CH2:42][CH3:43])(=[O:41])=[O:40])=[CH:34][CH:33]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([O:31][C:32]2[CH:33]=[CH:34][C:35]([N:38]([CH2:5]/[CH:6]=[CH:7]/[C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=3)[S:39]([CH2:42][CH3:43])(=[O:41])=[O:40])=[CH:36][CH:37]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 18542728HCID 18542728, compoundHCID 86595369HCID 86595369, compound

Product 1

HCID 18542622HCID 18542622, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 11776TriphenylphosphineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of [3-(3-cyanophenyl)-2-(E)-propenyl]ethyl carbonate (1.04 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 (0.077 g) and triphenylphosphine (0.039 g) and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using dichloromethane/ethyl acetate=8/1 as an eluant to give the desired compound (1.57 g, yield quantitative) as a pale yellow oil.

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-38707e4d0a744d5fbcdeec451324f485
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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