HCID 131727738, compound → HCID 131727737, compound

HRID 473528Notes

Reaction equation

HRID 473528 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:91]=[CH:90][C:89]2[C:84](=[CH:85][CH:86]=[CH:87][CH:88]=2)[CH:83]=1)[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:47]=[CH:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=1>C1COCC1>[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:91]=[CH:90][C:89]2[C:84](=[CH:85][CH:86]=[CH:87][CH:88]=2)[CH:83]=1)[CH2:2][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:47]=[CH:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=1

Participants

3

Reactant 1

HCID 131727738HCID 131727738, compound

Product 1

HCID 131727737HCID 131727737, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10% Cd/Pb couple (455 mg, 3.71 mmol, 26 eq) was added to a rapidly stirring mixture of 17 (190 mg, 0.14 mmol), THF (3.2 mL) and 1 N NH4OAc (3.2 mL). The reaction mixture was allowed to stir for 6.5 hours when TLC showed the incomplete consumption of the starting material and formation of side products. The solids were filtered and rinsed with H2O and MeOH. Excess solvent was removed and the residue was diluted with H2O (25 mL) and DCM (25 mL). The aqueous layer was extracted with DCM (3×25 mL) and the organic extracts were combined, washed with brine (50 mL) and dried (MgSO4). Filtration and evaporation of solvent afforded the crude product which was purified by flash column chromatography (99:1 v/v CHCl3/MeOH then gradient to 98:2 v/v CHCl3/MeOH) to afford 18 as a yellow glass (38 mg, 36%): 1H NMR (400 MHz, CDCl3) δ 7.85 (d, 2H, J=3.9 Hz, H11), 7.77-7.65 (m, 6H, Harom), 7.59-7.50 (m, 6H, H3 and Harom), 7.47 (s, 2H, H6), 7.44-7.33 (m, 4H, Harom), 6.82 (s, 2H, H9), 4.42-4.32 (m, 2H, H11a), 4.31-4.14 (m, 4H, OCH2CH2CH2O), 3.89 (s, 6H, OCH3×2), 3.69-3.56 (m, 2H, H1), 3.50-3.37 (m, 2H, H1), 2.45-2.29 (m, 2H, OCH2CH2CH2O).

Workup

  1. stirringto stir for 6.5 hours when TLC
  2. customthe incomplete consumption of the starting material and formation of side products
  3. filtrationThe solids were filtered
  4. washrinsed with H2O and MeOH
  5. customExcess solvent was removed
  6. additionthe residue was diluted with H2O (25 mL) and DCM (25 mL)
  7. extractionThe aqueous layer was extracted with DCM (3×25 mL)
  8. washwashed with brine (50 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 (99:1 v/v CHCl3/MeOH

Sources & evidence

ORD record
ord-e30c18fd351b4a0c8388fc1a1700cfb6
Source dataset
uspto-grants-2014_01
Patent number
US08633185B2

Reaction notes

Loading…