Triethylamine → HCID 69598118、化合物

HRID 724590ノート

反応式

HRID 724590 の反応式
Cl.[NH2:2][C@@H:3]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:23](=[O:25])(=[O:24])[N:22](C(C)(C)C)[C:21](=[O:30])[CH:20]=2)=[CH:15][CH:14]=1)[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:5].[N:31]([C@@H:34]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:35]([O:37]C)=[O:36])=[C:32]=[O:33].C(N(CC)CC)C>CN(C)C=O>[CH2:7]([NH:6][C:4]([C@@H:3]([NH:2][C:32](=[O:33])[NH:31][C@@H:34]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:35]([OH:37])=[O:36])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:23](=[O:25])(=[O:24])[NH:22][C:21](=[O:30])[CH:20]=2)=[CH:15][CH:14]=1)=[O:5])[CH2:8][CH2:9][CH2:10][CH3:11]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 1514293Methyl N-(oxomethylidene)phenylalaninateHCID 69597981HCID 69597981、化合物

生成物 1

HCID 69598118HCID 69598118、化合物収率 15.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A solution of 9-E (150 mg, 0.33 mmol), methyl (S)-(−)-2-isocyanato-3-phenylpropionate (120 μL, 0.66 mmol), and triethylamine (140 μL, 0.99 mmol) in dimethylformamide (2 mL) was stirred at 25° C. for 16 h. The reaction mixture was treated with Triamine-3 functionalized silica gel (1.2 mmol) and stirred for 1 h. The reaction mixture was filtered through a short plug of silica gel and washed with ethyl acetate (10 mL). The filtrate was concentrated and used without further purification. The crude product was dissolved in trifluoroacetic acid (10 mL) and heated at 70° C. for 16 h. The reaction mixture was concentrated and purified using preparative LCMS to yield the product (29 mg, 15%) as a white solid. 1H NMR (500 MHz, CD3OD): δ 7.83 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.3 Hz, 2H), 2H), 7.31–7.28 (m, 2H), 7.25–7.22 (m, 1H), 7.18 (dd, J=8.3, 1.5 Hz, 2H), 7.02 (s, 1H), 4.53 (dd, J=7.8, 5.9 Hz, 1H), 4.44 (dd, J=7.3, 6.8 Hz, 1H), 3.69 (s, 3H), 3.19–3.04 (m, 4H), 3.00–2.94 (m, 2H), 1.42–1.35 (m, 2H), 1.34–1.28 (m, 2H), 1.24–1.19 (m, 2H), 0.90 (t, J=7.3 Hz, 3H); LCMS found for C28H35N4O7S (M+H)+: m/z=571.

後処理

  1. filtrationThe reaction mixture was filtered through a short plug of silica gel
  2. washwashed with ethyl acetate (10 mL)
  3. concentrationThe filtrate was concentrated
  4. customused without further purification
  5. dissolutionThe crude product was dissolved in trifluoroacetic acid (10 mL)
  6. concentrationThe reaction mixture was concentrated
  7. custompurified

出典と根拠

ORDレコード
ord-29ca3fdd07b24da1a3e48b7ee73f56be
出典データセット
uspto-grants-2006_11
特許番号
US07141596B2

反応ノート

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