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

HRID 899865

반응식

HRID 899865 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-f47c460ec7e348ac82cab9f315f3f4cf
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07355069B2

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