Sodium Ascorbate → HCID 86661706, compound

HRID 532082Notes

Reaction equation

HRID 532082 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27]OCCOCCOCCOCC#C)([O-:3])=[O:2].[N:41]([CH2:44][CH2:45][CH2:46][CH2:47][C@H:48]([NH:56][C:57](=[O:76])[NH:58][C@@H:59]([CH2:67][CH2:68][C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])[C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[N+:42]=[N-:43].O=[C:78]1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.C(O)(C)(C)C.S([O-])([O-])(=O)=O.[Cu+2]>[C:52]([O:51][C:49](=[O:50])[C@@H:48]([NH:56][C:57](=[O:76])[NH:58][C@@H:59]([CH2:67][CH2:68][C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])[C:60]([O:62][C:63]([CH3:64])([CH3:65])[CH3:66])=[O:61])[CH2:47][CH2:46][CH2:45][CH2:44][N:41]1[CH:78]=[C:27]([CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][NH:13][C:5]2[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[N:43]=[N:42]1)([CH3:55])([CH3:54])[CH3:53]

Participants

7

Reactant 3

HCID 23667548Sodium AscorbateHCID 580788652,4-Dinitro-N-3,6,9,12,15,18,21,24-octaoxaheptacos-26-yn-1-ylbenzenamineHCID 86661707HCID 86661707, compound

Product 1

HCID 86661706HCID 86661706, compoundYield 265.3%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a mixture of 10 (76 mg, 0.145 mmol, 1.0 equiv) and 14 (74.4 mg, 0.145 mmol, 1.0 equiv.) in water (1 mL) and tert-butanol (1 mL) in a 5 ml μwave reaction tube was added sodium ascorbate (7 mg, 0.036 mmol, 0.25 equiv.) and aqueous solution of 0.1 M copper (II) sulfate (0.0725 ml, 0.00725 mmol, 0.05 equiv.). The tube was capped, and subjected to microwave radiation for 10 minutes at 110° C. The reaction was then concentrated and redissolved in trifluoroacetic acid (2 mL) and dichloromethane (1 mL) in a 5 ml microwave reaction tube. The tube was capped and subjected to microwave radiation for 2 m at 70° C. The resulting reaction mixture was concentrated under reduced pressure, chromatographed using HPLC, and concentrated to yield 3 (87 mg, 58% yield) as a yellow oil. IR (thin film/NaCl) 3359 (w), 2925 (s), 1737 (s), 1622 (m), 1170 (s) cm−1; 1HNMR (100 MHz, MeOD) δ 9.07 (d, J=2.7 Hz, 1H), 8.33 (dd, J=2.7, 9.6 Hz, 1H), 8.03 (s, 1H), 7.27 (d, J=9.6 Hz, 1H), 4.66 (s, 2H), 4.45 (t, J=7 Hz, 2H), 4.35-4.28 (m, 2H), 3.83 (t, J=7 Hz, 2H), 3.73-3.61 (m, 32H), 2.44-2.36 (m, 2H), 2.17-2.08 (m, 1H), 1.99-1.82 (m, 4H), 1.71-1.64 (m, 1H), 1.46-1.38 (m, 2H); 13CNMR (125 MHz, MeOD) δ 176.4, 176.1, 175.7, 160.0, 149.9, 145.9, 137.0, 131.5, 131.0, 125.2, 124.7, 116.1, 71.6, 71.6, 71.5, 71.5, 70.9, 69.9, 64.8, 53.7, 53.5, 51.2, 44.1, 32.8, 31.1, 30.6, 28.8, 23.4 ppm; HRMS (ES+) calc'd for C37H58N8O19 (M+H) m/z 919.389098. Found 919.38801. NAALADase Inhibition Experiments

Workup

  1. customμwave reaction tube
  2. customThe tube was capped
  3. customfor 10 minutes
  4. customat 110° C
  5. concentrationThe reaction was then concentrated
  6. dissolutionredissolved in trifluoroacetic acid (2 mL)
  7. customThe tube was capped
  8. customat 70° C
  9. customThe resulting reaction mixture
  10. concentrationwas concentrated under reduced pressure
  11. customchromatographed
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-9862ce719a124170ba4eb7b215dea581
Source dataset
uspto-grants-2014_10
Patent number
US08852630B2

Reaction notes

Loading…