Triethylamine → HCID 54280683、化合物

HRID 1736618ノート

反応式

HRID 1736618 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

HCID 54280683HCID 54280683、化合物収率 53.3%

試薬・触媒・溶媒 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e884642c698549d48599dd3198ed55c2
出典データセット
uspto-grants-1996_07
特許番号
US05541286

反応ノート

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