HCID 131727742, compound → HCID 131727741, compound

HRID 1434470Notes

Reaction equation

HRID 1434470 reaction equation
[CH2:1]([O:48][CH:49]1[C@H:53]2[C@H:54](O[Si](C(C)(C)C)(C)C)[N:55](C(OCC(Cl)(Cl)Cl)=O)[C:56]3[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[CH:60][C:57]=3[C:58](=[O:59])[N:52]2[CH:51]=[C:50]1[C:82]1[CH:83]=[C:84]2[C:89](=[CH:90][CH:91]=1)[N:88]=[CH:87][CH:86]=[CH:85]2)[CH2:2][CH2:3][O:4][CH:5]1[C@H:9]2[C@H:10](O[Si](C(C)(C)C)(C)C)[N:11](C(OCC(Cl)(Cl)Cl)=O)[C:12]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:13]=3[C:14](=[O:15])[N:8]2[CH:7]=[C:6]1[C:38]1[CH:39]=[C:40]2[C:45](=[CH:46][CH:47]=1)[N:44]=[CH:43][CH:42]=[CH:41]2>C1COCC1>[CH2:3]([O:4][CH:5]1[C@@H:9]2[CH:10]=[N:11][C:12]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:13]=3[C:14](=[O:15])[N:8]2[CH:7]=[C:6]1[C:38]1[CH:39]=[C:40]2[C:45](=[CH:46][CH:47]=1)[N:44]=[CH:43][CH:42]=[CH:41]2)[CH2:2][CH2:1][O:48][CH:49]1[C@@H:53]2[CH:54]=[N:55][C:56]3[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[CH:60][C:57]=3[C:58](=[O:59])[N:52]2[CH:51]=[C:50]1[C:82]1[CH:83]=[C:84]2[C:89](=[CH:90][CH:91]=1)[N:88]=[CH:87][CH:86]=[CH:85]2

Participants

3

Reactant 1

HCID 131727742HCID 131727742, compound

Product 1

HCID 131727741HCID 131727741, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10% Cd/Pb couple (516 mg, 4.21 mmol, 25 eq) was added to a rapidly stirring mixture of 23 (234 mg, 0.17 mmol), THF (5 mL) and 1 N NH4OAc (5 mL). The reaction mixture was allowed to stir for 5 hours when TLC showed complete consumption of the starting material and formation of a small amount of side products. The solids were filtered and rinsed with H2O and a large amount of MeOH. Excess solvent was removed and the residue was diluted with H2O (35 mL) and CHCl3 (35 mL). The aqueous layer was extracted with CHCl3 (3×30 mL) and the organic extracts were combined, washed with brine (100 mL) and dried (MgSO4). Filtration and evaporation of solvent afforded the crude product which was purified by flash column chromatography (99.5:0.5 v/v CHCl3/MeOH then gradient to 96:4 v/v CHCl3/MeOH) to afford 24 as a yellow glass (44 mg, 33%): 1H NMR (400 MHz, CDCl3) δ 8.85 (dd, 2H, J=1.6, 4.2 Hz, Harom), 8.09 (d, 2H, J=7.6 Hz, Harom), 8.03 (d, 2H, J=9.0 Hz, Harom), 7.88 (d, 2H, J=3.9 Hz, H11), 7.82 (dd, 2H, J=1.8, 8.9 Hz, Harom), 7.24 (s, 2H, H3), 7.59 (s, 2H, Harom), 7.52 (s, 2H, H6), 7.48 (dd, 2H, J=4.3, 8.3 Hz, Harom), 6.88 (s, 2H, H9), 4.48-4.42 (m, 2H, H11a), 4.39-4.28 (m, 4H, OCH2CH2CH2O), 3.94 (s, 6H, OCH3×2), 3.76-3.63 (m, 2H, H1), 3.09-2.98 (m, 2H, H1), 2.46-2.43 (m, 2H, OCH2CH2CH2O).

Workup

  1. stirringto stir for 5 hours when TLC
  2. customconsumption of the starting material and formation of a small amount of side products
  3. filtrationThe solids were filtered
  4. washrinsed with H2O
  5. customExcess solvent was removed
  6. additionthe residue was diluted with H2O (35 mL) and CHCl3 (35 mL)
  7. extractionThe aqueous layer was extracted with CHCl3 (3×30 mL)
  8. washwashed with brine (100 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationFiltration and evaporation of solvent
  11. customafforded the crude product which
  12. customwas purified by flash column chromatography (99.5:0.5 v/v CHCl3/MeOH

Sources & evidence

ORD record
ord-b6ed28069c974f63b8b6b3904d178443
Source dataset
uspto-grants-2009_11
Patent number
US07612062B2

Reaction notes

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