HCID 89471697, compound → HCID 178483375, compound

HRID 1056931Notes

Reaction equation

HRID 1056931 reaction equation
[CH3:1][O:2][C:3]1[C:34]([O:35][CH2:36][CH2:37][CH2:38][O:39][C:40]2[C:41]([O:69][CH3:70])=CC3[C:49](=[O:50])[N:48]4[CH:51]=[C:52]([C:54]#[C:55][CH2:56][NH:57][CH3:58])[CH2:53][C@H:47]4[C:46](=O)[N:45](COCC[Si](C)(C)C)[C:44]=3[CH:68]=2)=[CH:33][C:6]2[N:7](COCC[Si](C)(C)C)[C:8](=O)[C@@H:9]3[CH2:15][C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)=[CH:13][N:10]3[C:11](=[O:12])[C:5]=2[CH:4]=1>C1COCC1>[CH3:70][O:69][CH2:41]/[C:40](/[O:39][CH2:38][CH2:37][CH2:36][O:35][C:34]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[C:11](=[O:12])[N:10]3[CH:13]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[CH2:15][C@H:9]3[CH:8]=[N:7][C:6]=2[CH:33]=1)=[CH:68]\[CH2:44]/[N:45]=[CH:46]\[C@@H:47]1[CH2:53][C:52]([C:54]#[C:55][CH2:56][NH:57][CH3:58])=[CH:51][N:48]1[CH:49]=[O:50]

Participants

3

Reactant 1

HCID 89471697HCID 89471697, compound

Product 1

HCID 178483375HCID 178483375, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Compound 2 (0.041 g, 0.04 mmol) was dissolved in anhydrous THF (3.8 mL) under an argon atmosphere and cooled to −78° C. in an acetone-dry ice bath. LiEt3BH (0.25 mL of a 1M solution in THF, 0.35 mmol, 6 eq) was added to the mixture, and the reaction was stirred at −78° C. for 40 minutes. The reaction was quenched with H2O (3 mL) and after addition of brine (3 mL) the aqueous phase was extracted (DCM, 9 mL-methanol 1 mL), dried (MgSO4) and the solvent was removed by rotary evaporation under reduced pressure. The crude was dissolved in a mixture of ethanol (3 mL), DCM (1.5 mL) and H2O (1.5 mL) and silica gel was added to the mixture. The reaction was stirred for four days at room temperature under an atmosphere of Argon. The mixture was filtered over a sinter funnel washing with a mixture of DMC (140 mL) and methanol (15 mL). The organic phase was washed with brine (200 mL), dried (MgSO4) and the solvent was removed by rotary evaporation under reduced pressure. The resulting brown solid was purified by flash column chromatography (silica gel, gradient 90% DCM-10% methanol). Compound 3 was obtained as a brown solid (0.029 g, 59%); Rf 0.11 [8% methanol in DCM]; LC-MS (5 min) 2.47 min, ES+ 702.28.

Workup

  1. customThe reaction was quenched with H2O (3 mL)
  2. additionafter addition of brine (3 mL) the aqueous phase
  3. extractionwas extracted (DCM, 9 mL-methanol 1 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed by rotary evaporation under reduced pressure
  6. dissolutionThe crude was dissolved in a mixture of ethanol (3 mL), DCM (1.5 mL) and H2O (1.5 mL) and silica gel
  7. additionwas added to the mixture
  8. stirringThe reaction was stirred for four days at room temperature under an atmosphere of Argon
  9. filtrationThe mixture was filtered over a sinter funnel
  10. washwashing with a mixture of DMC (140 mL) and methanol (15 mL)
  11. washThe organic phase was washed with brine (200 mL)
  12. dry with materialdried (MgSO4)
  13. customthe solvent was removed by rotary evaporation under reduced pressure
  14. customThe resulting brown solid was purified by flash column chromatography (silica gel, gradient 90% DCM-10% methanol)

Sources & evidence

ORD record
ord-db8260f30d37484f982a6b2e4af2f215
Source dataset
uspto-grants-2016_07
Patent number
US09399641B2

Reaction notes

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