HCID 131727740, compound → HCID 131727739, compound

HRID 473529Notes

Reaction equation

HRID 473529 reaction equation
[CH2:1]([O:43][CH:44]1[C@H:48]2[C@H:49](O[Si](C(C)(C)C)(C)C)[N:50](C(OCC(Cl)(Cl)Cl)=O)[C:51]3[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][C:52]=3[C:53](=[O:54])[N:47]2[CH:46]=[C:45]1[C:77]1[S:78][CH:79]=[CH:80][CH:81]=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[S:39][CH:40]=[CH:41][CH:42]=1>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[S:39][CH:40]=[CH:41][CH:42]=1)[CH2:2][CH2:1][O:43][CH:44]1[C@@H:48]2[CH:49]=[N:50][C:51]3[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][C:52]=3[C:53](=[O:54])[N:47]2[CH:46]=[C:45]1[C:77]1[S:78][CH:79]=[CH:80][CH:81]=1

Participants

3

Reactant 1

HCID 131727740HCID 131727740, compound

Product 1

HCID 131727739HCID 131727739, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10% Cd/Pb couple (288 mg, 2.35 mmol, 20 eq) was added to a rapidly stirring mixture of 20 (154 mg, 0.12 mmol), THF (3 mL) and 1 N NH4OAc (3 mL). The reaction mixture was allowed to stir for 3 hours when TLC showed complete consumption of the starting material. The solids were filtered and rinsed with H2O and DCM. The aqueous layer was extracted with DCM (3×15 mL) and the organic extracts were combined, washed with brine (40 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 21 as a yellow glass (59 mg, 72%): 1H NMR (400 MHz, CDCl3) δ 7.90 (d, 2H, J=4.0 Hz, H11), 7.51 (s, 2H, H6), 7.36 (s, 2H, H3), 7.22 (d, 2H, J=5.2 Hz, Harom), 7.02 (dd, 2H, J=3.6, 5.0 Hz, Harom), 6.98 (d, 2H, J=3.4 Hz, Harom), 6.88 (s, 2H, H9), 4.43-4.23 (m, 6H, H11a and OCH2CH2CH2O), 3.94 (s, 6H, OCH3×2), 3.59 (ddd, 2H, J=2.0, 11.5, 16.0 Hz, H1), 2.85 (ddd, 2H, J=1.5, 5.2, 16.0 Hz, H1), 2.49-2.40 (m, 2H, OCH2CH2CH2O).

Workup

  1. stirringto stir for 3 hours when TLC
  2. customconsumption of the starting material
  3. filtrationThe solids were filtered
  4. washrinsed with H2O and DCM
  5. extractionThe aqueous layer was extracted with DCM (3×15 mL)
  6. washwashed with brine (40 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and evaporation of solvent
  9. customafforded the crude product which
  10. customwas purified by flash column chromatography (99:1 v/v CHCl3/MeOH

Sources & evidence

ORD record
ord-42d4cd0af85a455ebf94bf1b6ab34111
Source dataset
uspto-grants-2014_01
Patent number
US08633185B2

Reaction notes

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