huagongshe.com
HRID530146

反应详情

EQUATION

反应方程式

HRID 530146 的结构方程式

REACTANTS

反应物

1
结构：CC(C)(C)OC(=O)NCCOCCOCCOCCNC(=O)CC[C@H](NC(=O)c1ccc(NCc2cnc3nc(N)nc(O)c3n2)cc1)C(=O)OC(C)(C)C
HCID178453758

未命名化合物

PRODUCTS

生成物

1
结构：NCCOCCOCCOCCNC(=O)CC[C@H](NC(=O)c1ccc(NCc2cnc3nc(N)nc(O)c3n2)cc1)C(=O)O
HCID178511412

未命名化合物

收率 36%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：Cl
溶剂HCID313

Hydrochloric Acid

ClH

2 次

PROCEDURE

实验过程

To (S)-tert-butyl 21-(4-((2-amino-4-hydroxypteridin-6-yl)methylamino)benzamido)-2,2-dimethyl-4,18-dioxo-3,8,11,14-tetraoxa-5,17-diazadocosan-22-oate (425 mg, 0.551 mmol) aqueous 6 M hydrochloric acid (10 mL) was added. The reaction was stirred at ambient temperature for 16 hours. After this time, the reaction was not complete. The reaction was concentrated under reduced pressure and dissolved in N,N-dimethylformamide (5 mL). To the resulting mixture TFA (7 mL) was added and reaction mixture stirred at ambient temperature for 16 hours. After this time, the reaction was diluted with 6 M aqueous hydrochloric acid (50 mL) and filtered through diatomaceous earth. The filter cake was rinsed with methanol (40 mL), and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by semi-preparative HPLC (100:0 to 3:7 H2O/CH3CN with 0.05% TFA over 25 min). Further purification by semi-preparative HPLC (100:0 to 3:7 H2O/CH3CN with 0.05% TFA over 25 min) was required to obtain pure (S)-1-amino-16-(4-((2-amino-4-hydroxypteridin-6-yl)methylamino)benzamido)-13-oxo-3,6,9-trioxa-12-azaheptadecan-17-oic acid (121 mg, 36%) as a yellow solid that was obtained via lyophilization: 1H NMR (300 MHz, DMSO-d6) δ 10.88 (vbs, 1H), 8.65 (s, 1H), 8.20 (d, J=6.6 Hz, 1H), 7.95-7.89 (m, 1H), 7.78 (bs, 2H), 7.65 (d, J=8.7 Hz, 2H), 7.00-6.90 (m, 2H), 6.64 (d, J=8.7 Hz, 2H), 4.49 (s, 2H), 4.31-4.28 (m, 1H), 3.78-3.45 (m, 12H), 3.43-3.35 (m, 2H), 3.28-3.20 (m, 2H), 3.02-2.98 (m, 2H), 2.23-2.17 (m, 2H), 2.12-2.00 (m, 1H), 1.99-1.87 (m, 1H); ESI MS m/z=614 [M−H]−.

WORKUP

后处理

  1. concentrationThe reaction was concentrated under reduced pressure
  2. dissolutiondissolved in N,N-dimethylformamide (5 mL)
  3. additionTo the resulting mixture TFA (7 mL) was added
  4. customreaction mixture
  5. stirringstirred at ambient temperature for 16 hours
  6. filtrationfiltered through diatomaceous earth
  7. washThe filter cake was rinsed with methanol (40 mL)
  8. customthe filtrate obtained
  9. concentrationwas concentrated under reduced pressure
  10. customThe residue obtained
  11. customwas purified by semi-preparative HPLC (100:0 to 3:7 H2O/CH3CN with 0.05% TFA over 25 min)
  12. customFurther purification by semi-preparative HPLC (100:0 to 3:7 H2O/CH3CN with 0.05% TFA over 25 min)