Triethylamine → 3-Ethyl-5-(3-hydroxy-benzylcarbamoyl)-thiophene-2-carboxylic acid methyl ester

HRID 1952628노트

반응식

HRID 1952628 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:12]([OH:14])=O)=[CH:8][C:9]=1[CH2:10][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.[NH2:56][CH2:57][C:58]1[CH:59]=[C:60]([OH:64])[CH:61]=[CH:62][CH:63]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:12](=[O:14])[NH:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([OH:64])[CH:59]=2)=[CH:8][C:9]=1[CH2:10][CH3:11])=[O:4]

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 682264933-Ethyl-thiophene-2,5-dicarboxylic acid 2-methyl ester

생성물 1

HCID 682269473-Ethyl-5-(3-hydroxy-benzylcarbamoyl)-thiophene-2-carboxylic acid methyl ester수율 38%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-Ethyl-thiophene-2,5-dicarboxylic acid 2-methyl ester (250 mg, 1.17 mmol) in anhydrous DMF (10 mL) was added triethylamine (0.50 mL, 3.51 mmol), HBTU (0.67 g, 1.76 mmol), HOBT (190 mg, 1.40 mmol), and 3-Aminomethyl phenol (160 mg, 1.29 mmol). The mixture was stirred at room temperature 2 d, 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 0-50% EtOAc in hexane to afford the desired product (0.140 g, 38% 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 0-50% EtOAc in hexane

출처 및 근거

ORD 기록
ord-3b3557961e394d5a880d5572db2b5e2e
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404859B2

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