Diisopropylethylamine → Methyl (2S)-3-(4-biphenylyl)-2-[(2-isopropoxy-3,4-dioxocyclobut-1-enyl)amino]propanoate

HRID 1281909

반응식

HRID 1281909 반응식
Cl.[NH2:2][C@@H:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5].[CH:21]([O:24][C:25]1[C:26](=O)[C:27](=[O:33])[C:28]=1[O:29]C(C)C)([CH3:23])[CH3:22].CCN(C(C)C)C(C)C>CO>[C:12]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:14][C:9]([CH2:8][C@H:3]([NH:2][C:26]2[C:27](=[O:33])[C:28](=[O:29])[C:25]=2[O:24][CH:21]([CH3:23])[CH3:22])[C:4]([O:6][CH3:7])=[O:5])=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 1823143,4-Diisopropoxy-3-cyclobutene-1,2-dioneHCID 45357110methyl (2S)-2-amino-3-(4-phenylphenyl)propanoate hydrochloride

생성물 1

HCID 86583676Methyl (2S)-3-(4-biphenylyl)-2-[(2-isopropoxy-3,4-dioxocyclobut-1-enyl)amino]propanoate수율 64.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of methyl (2S)-2-amino-3-(4-biphenylyl)-propanoate hydrochloride (415 mg, 1142 mmol),3,4-diisopropoxy-3-cyclobutene-1,2-dione (281 mg, 1.42 mmol), DIPEA (247 μl, 1.42 mmol) and MeOH (10 ml) was stirred at room temperature overnight. The solvent was removed in vacuo and the residue purified by column chromatography (SiO2; DCM/MeOH, 98:2) to give the title compound (358 mg). δH (DMSO-d6, 390K) 8.50 (1H, d, J 8.0 Hz), 7.63-7.56 (4H, m), 7.47-7.42 (2H, m), 7.36-7.32 (3H, m), 5.24-5.18 (1H, m), 4.80-4.75 (1H, m), 3.74 (3H, s), 3.31 (1H, dd, J 14.2, 5.2 Hz), 3.13 (1H, dd, J, 14.2, 9.4 Hz), 1.38 (3H, d, J 6.0 Hz), 1.37 (3H, d, J 6.1 Hz); m/z (ES+, 70 V) 394 (MH+).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by column chromatography (SiO2; DCM/MeOH, 98:2)

출처 및 근거

ORD 기록
ord-1cf98b4fc9a14b00a78dc177bfce27af
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06455539B2

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