3-(4-Hydroxyphenyl)propionic acid → N-benzyl-N-hexyl-3-(4-hydroxyphenyl)propanamide

HRID 899865

反応式

HRID 899865 の反応式
[CH2:1]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([OH:26])=O)=[CH:18][CH:17]=1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:8]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:24](=[O:26])[CH2:23][CH2:22][C:19]1[CH:18]=[CH:17][C:16]([OH:15])=[CH:21][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

7

反応物 5

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 485395Benzenemethanamine, N-hexyl-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

生成物 1

HCID 69120664N-benzyl-N-hexyl-3-(4-hydroxyphenyl)propanamide収率 71.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-hexylbenzylamine (0.6 g, 3.136 mmol) and 3-(4-hydroxyphenyl)propionic acid (0.52 g 3.136 mmol) were mixed in DMF (10 ml) and the mixture was cooled. HOBT (0.424 g, 3.136 mmol) and the TBTU (1 g, 3.136 mmol) reagent were added followed by DIPEA (1.216 g, 9.409 mmol). The mixture was stirred at room temperature overnight and then evaporated. The resulting mixture was partitioned between ethyl acetate and sodium hydrogencarbonate aqueous solution (sat.). The aqueous portion was extracted with ethyl acetate and the combined organic extracts dried with magnesium sulphate and then evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 5 g/25 ml) using ethyl acetate/heptane (10:90, then 25:75) as eluant gave 760 mg the desired product, yield 71%.

後処理

  1. temperaturethe mixture was cooled
  2. customevaporated
  3. customThe resulting mixture was partitioned between ethyl acetate and sodium hydrogencarbonate aqueous solution (sat.)
  4. extractionThe aqueous portion was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts dried with magnesium sulphate
  6. customevaporated

出典と根拠

ORDレコード
ord-f47c460ec7e348ac82cab9f315f3f4cf
出典データセット
uspto-grants-2008_04
特許番号
US07355069B2

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