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

HRID 1281909ノート

反応式

HRID 1281909 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-1cf98b4fc9a14b00a78dc177bfce27af
出典データセット
uspto-grants-2002_09
特許番号
US06455539B2

反応ノート

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