Triethylamine → HCID 69598118, 화합물

HRID 724590노트

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HRID 724590 반응식
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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 1514293Methyl N-(oxomethylidene)phenylalaninateHCID 69597981HCID 69597981, 화합물

생성물 1

HCID 69598118HCID 69598118, 화합물수율 15.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-29ca3fdd07b24da1a3e48b7ee73f56be
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141596B2

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