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Triethylamine → 5-(3-Hydroxy-benzylcarbamoyl)-3-isopropyl-thiophene-2-carboxylic acid methyl ester

HRID 1952616
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HRID 1952616 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13]([OH:15])=O)=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11])=[O:4].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[NH2:57][CH2:58][C:59]1[CH:60]=[C:61]([OH:65])[CH:62]=[CH:63][CH:64]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13](=[O:15])[NH:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([OH:65])[CH:60]=2)=[CH:8][C:9]=1[CH:10]([CH3:11])[CH3:12])=[O:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 7358943-(Aminomethyl)phenolHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 682270964-Isopropyl-5-(methoxycarbonyl)thiophene-2-carboxylic acid

생성물 1

HCID 68226555
5-(3-Hydroxy-benzylcarbamoyl)-3-isopropyl-thiophene-2-carboxylic acid methyl ester
수율 44%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-Isopropyl-thiophene-2,5-dicarboxylic acid 2-methyl ester (110 mg, 0.48 mmol) in anhydrous DMF (5 mL) was added triethylamine (0.20 mL, 1.45 mmol), HBTU (0.27 g, 0.72 mmol), HOBT (78 mg, 0.58 mmol), and 3-Aminomethyl phenol (65 mg, 0.53 mmol). The mixture was stirred at room temperature 15 h, then quenched by pouring into EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 0-60% EtOAc in hexane to afford the desired product (0.070 g, 44% yield).

후처리

  1. customquenched
  2. additionby pouring into EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography with 0-60% EtOAc in hexane

출처 및 근거

ORD 기록
ord-58c73026e95a476e84eaa760ba7841e7
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08404859B2

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