Triethylamine → HCID 54280683, 화합물

HRID 1736618노트

반응식

HRID 1736618 반응식
[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]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 73688Methyl butadienecarboxylateHCID 70183002-Bromo-N-(tert-butoxycarbonyl)benzylamine

생성물 1

HCID 54280683HCID 54280683, 화합물수율 53.3%

시약·촉매·용매 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e884642c698549d48599dd3198ed55c2
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05541286

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