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HRID727116

反应详情

EQUATION

反应方程式

HRID 727116 的结构方程式

REACTANTS

反应物

4
结构：[Br-].[K+]
HCID253877

Potassium bromide

BrK

结构：O=Cc1ccc2c(n1)C(=O)C(NC(=O)CCl)=CC2=O
HCID11572689

未命名化合物

结构：CC(C)CCOC(=O)[C@@H](N)Cc1c[nH]c2ccccc12
HCID11594264

未命名化合物

结构：COC(=O)[C@@H](N)C(C)c1c[nH]c2ccccc12
HCID14284053

未命名化合物

PRODUCTS

生成物

1
结构：CC(C)CCOC(=O)c1cc2c([nH]c3ccccc32)c(-c2ccc3c(n2)C(=O)C(NC(=O)CCl)=CC3=O)n1
HCID11642266

未命名化合物

收率 27%

CONDITIONS

反应条件

温度
76 °C

PROCEDURE

实验过程

In a 100 ml. three-necked, round-bottomed flask equipped with a reflux condenser, flowing argon and a magnetic bar, 7-chloro-acetamido-2-formylquinoline-5,8-dione (24) (prepared as described in Example 24) (0.0500 g., 0.18 mmol), L-tryptophan isoamyl ester (37) (prepared as described in Example 37) (0.0490 g., 0.18 mmol), and 75 ml. of dried and distilled xylene were slowly heated to 76° C. over a five-hour period. Upon the first detection of the formation of a light-colored precipitate, the mixture was filtered hot. The filtrate was concentrated under reduced pressure to about 10 ml. The filtrate was stored in a refrigerator overnight during which a considerable amount of a dark orange-brown solid formed. This was filtered and washed with cold ethyl acetate giving 25.5 mg. of the crude product (a yield of 27%). The filtrate was further concentrated which, upon cooling, yielded an additional 15 mg. of the product (16% yield, total yield 43%): mp. 280-284° C.; 1H NMR (CDCl3) δ 1.05 (6H, d, J=6.3 Hz., (CH3)2), 1.76-1.95 (3H, m, COOCH2CH2CH), 4.29 (2H, s, C-7NHCOCH2Cl), 4.52 (2H, t, J=6.8 Hz., COOCH2), 7.39 (1H, dd, J=8.0 Hz., J=8.0 Hz., C-11'H), 7.66 (1H, dd, J=8.0 Hz., J=8.0 Hz., C-10'H), 7.78 (1H, d, J=8.0 Hz., C-9'H), 7.95 (1H, s, C-6H), 8.23 (1H, d, J=8.0 Hz., C-12'H), 8.54 (1H, d, J=8.3 Hz., C-3H), 8.93 (1H, s, C-3'H), 9.18 (1H, d, J=8.3 Hz., C-4H), 9.56 (1H, br s, C-7NH), 11.76 (1H, br s, NH); IR (KBr) vmax 3336, 2957, 2929, 2908, 2871, 1713, 1680, 1651, 1588, 1520, 1337, 1308, 1265, 1219, 1119, 738 cm1 ; EIMS, m/e (relative intensity) 530/532 (M+, 2.4/1, 45), 496 (58), 480 (6), 454 (39), 416 (83), 382 (95), 366 (15), 340 (base); HRMS, m/e for C28 H23ClN4O5 calculated 530.135698, found 530.135781.

WORKUP

后处理

  1. customthree-necked, round-bottomed flask equipped with a reflux condenser
  2. customof dried
  3. distillationdistilled xylene
  4. filtrationUpon the first detection of the formation of a light-colored precipitate, the mixture was filtered hot
  5. concentrationThe filtrate was concentrated under reduced pressure to about 10 ml
  6. customwas stored in a refrigerator overnight during which
  7. customformed
  8. filtrationThis was filtered
  9. washwashed with cold ethyl acetate giving 25.5 mg
  10. concentrationThe filtrate was further concentrated which
  11. temperatureupon cooling
  12. customyielded an additional 15 mg