Triethylamine → HCID 54280683, compound

HRID 1736618Notes

Reaction equation

HRID 1736618 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1Br)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:24]([O:30][CH3:31])(=[O:29])[CH:25]=[CH:26][CH:27]=[CH2:28]>O.CCOCC.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]([O:30][CH3:31])=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 736882,4-Pentadienoic acid, methyl esterHCID 70183002-Bromo-N-(tert-butoxycarbonyl)benzylamine

Product 1

HCID 54280683HCID 54280683, compoundYield 53.3%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3.0 g (10.5 mmol) of 1-(tert-butoxycarbonylaminomethyl)-2-bromobenzene, 4.5 ml (32.3 mmol) of triethylamine, 1.82 ml (15.7 mmol) of methyl 2,4-pentadienoate and 0.2 g (0.28 mmol) of bis (triphenylphosphine) palladium (II) chloride was sealed in a heavy-walled Pyrex, Teflon screw-capped flask and heated at 100° C. for 40 hours. After being cooled to 25° C. the reaction mixture was diluted with 150 ml of water and 50 ml of ether. The aqueous phase was extracted with ether. The combined ether extracts were washed with water and brine, dried (Na2SO4) and concentrated. The residue was chromatographed on a silica gel column that was eluted with a 5 to 10% gradient of ethyl acetate in hexane to give 1.6 g (53.3%) of colorless needles, mp 96°-97.5° C. after recrystallization from 1:3 ether:hexane.

Workup

  1. temperatureAfter being cooled to 25° C. the reaction mixture
  2. extractionThe aqueous phase was extracted with ether
  3. washThe combined ether extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a silica gel column that
  7. washwas eluted with a 5 to 10% gradient of ethyl acetate in hexane

Sources & evidence

ORD record
ord-e884642c698549d48599dd3198ed55c2
Source dataset
uspto-grants-1996_07
Patent number
US05541286

Reaction notes

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