HRID1297524

反应详情

EQUATION

反应方程式

HRID 1297524 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

To a stirred, ice-bath cooled mixture of tert-butyl 4-[N-(5-(2-benzyloxy-ethanoylamino)-6-cyanoindan-1-yl)amino]benzoate (3.77 g, 7.59 mmol), EtOH (70 ml), and H2O (11 ml) was added 30% H2O2 (8.05 ml) followed by granulated NaOH pellets (0.640 g, 16.0 mmol). The reaction mixture was stirred at 0° C. for 10 min, then placed in an oil-bath preheated to 55° C. and stirred at this temperature for 1 hour. The solvents were then removed in vacuo; the residue was treated with H2O (80 ml) and the pH was adjusted to ˜5 with 1N HCl. The pale yellow solid was collected by filtration, washed with H2O and dried in vacuo over P2O5 (3.56 g, 95%); mp 194-195° C.; 1H-NMR (250 MHz, DMSO-d6, TMS) 1.52 (s, 9H, C(CH3)3), 1.90 (m), 2.62 (m) (1H each, 7-CH), 2.90-3.17 (m, 2H, 8-CH2), 4.43, 4.60 (2×s, 2H each, PhCH2 and OCH2CO), 5.18 (q, J=7.43 Hz, 1H, 6-CH), 6.79 (d, J=8.8 Hz, 2H, 3′,5′-ArH), 6.87 (d, J=8.0 Hz, 1H, N10—H), 7.34 (m, 5H, PhCH2), 7.54, 7.92 (2×s, 1H each, 5-H and 9-H), 7.68 (d, J=8.9 Hz, 2H, 2′,6′-ArH), 12.20 (s, 1H, CONH); MS (ESI, m/z) 520 {(M+Na)+, 90%,}, 498 {(M+H)+, 100%}; Found: C, 72.13; H, 6.25; N, 8.38; C30H31N3O4 requires C, 72.41; H, 6.28; N, 8.44%.

WORKUP

后处理

  1. temperatureTo a stirred, ice-bath cooled
  2. customplaced in an oil-bath
  3. custompreheated to 55° C.
  4. stirringstirred at this temperature for 1 hour
  5. customThe solvents were then removed in vacuo
  6. additionthe residue was treated with H2O (80 ml)
  7. filtrationThe pale yellow solid was collected by filtration
  8. washwashed with H2O
  9. dry with materialdried in vacuo over P2O5 (3.56 g, 95%)