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Triethylamine → HCID 86614670, compound

HRID 1433767
Notes
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Reaction equation

HRID 1433767 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[CH:10]([C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=1)[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:27]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH2:28].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9](=[O:26])[CH:10]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:19]1[CH:24]=[CH:23][C:22](/[CH:28]=[CH:27]/[S:29]([CH3:32])(=[O:31])=[O:30])=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 19354Methyl vinyl sulfoneHCID 80271Tri-o-tolylphosphineHCID 68620118HCID 68620118, compound

Product 1

HCID 86614670HCID 86614670, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 6342AcetonitrileSolvent

Procedure

(4-Bromo-phenyl)-tert-butoxycarbonylamino-acetic acid benzyl ester (1.5 g, 3.6 mmol), methyl vinyl sulfone (406 μL, 4.6 mmol), palladium(II) acetate (80 mg, 10 mol %), tri-o-tolylphosphine (217 mg, 20 mol %) and triethylamine (2.0 ml, 14.3 mmol) were combined in acetonitrile (18 mL), degassed and refluxed for 8 hours. Additional palladium(II) acetate (80 mg, 10 mol %) and tri-o-tolylphosphine (217 mg, 20 mol %) were added and refluxing continued overnight. The reaction was cooled, solvent removed in vacuo and the residue was purified by chromatography over silica gel gradient eluted from 20 to 90% v/v ethyl acetate in hexane to afford tert-butoxycarbonylamino-[4-((E)-2-methanesulfonyl-vinyl)-phenyl]-acetic acid benzyl ester (1.2 g, 75%).

Workup

  1. customdegassed
  2. temperaturerefluxed for 8 hours
  3. additionAdditional palladium(II) acetate (80 mg, 10 mol %) and tri-o-tolylphosphine (217 mg, 20 mol %) were added
  4. temperaturerefluxing continued overnight
  5. temperatureThe reaction was cooled
  6. customsolvent removed in vacuo
  7. customthe residue was purified by chromatography over silica gel gradient
  8. washeluted from 20 to 90% v/v ethyl acetate in hexane

Sources & evidence

ORD record
ord-58261898644d4049b6b31fbc4b0c4f31
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07612212B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes