Hydrochloric Acid → HCID 178450837, compound

HRID 1518388Notes

Reaction equation

HRID 1518388 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][CH2:7][C:8]1[C:9]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[N:10][C:11]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[C:17]([C:24](=[O:43])/[N:25]=[C:26]4\[S:27][C:28]5[CH:42]=[CH:41][CH:40]=[CH:39][C:29]=5[N:30]\4[CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[CH:12][CH:13]=1.Cl>C1COCC1>[O:1]=[CH:2][CH2:6][CH2:7][C:8]1[C:9]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[N:10][C:11]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[C:17]([C:24](=[O:43])/[N:25]=[C:26]4\[S:27][C:28]5[CH:42]=[CH:41][CH:40]=[CH:39][C:29]=5[N:30]\4[CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178450836HCID 178450836, compound

Product 1

HCID 178450837HCID 178450837, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
48 °C

Procedure

Compound 94D (1.47 g) was dissolved in THF (30 mL). To this solution was added 5% HCl (10 mL). The reaction mixture was heated at 48° C. for 90 min. After cooling to room temperature, the reaction mixture was quenched with sat. NaHCO3 solution until no more CO2 was released. The solution was concentrated under vacuum. The residue was re-dissolved in EtOAc, and treated with water (100 mL). The organic layer was separated, and the aqueous layer was extracted with additional EtOAc (three times). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under vacuum. The residue was purified with flash column chromatography on silica gel eluting with 7:3/Hex:EtOAc to give 1.10 g of the title compound 94E (80%): APCI (+)LC/MS: 673 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was quenched with sat. NaHCO3 solution until no more CO2
  3. concentrationThe solution was concentrated under vacuum
  4. dissolutionThe residue was re-dissolved in EtOAc
  5. additiontreated with water (100 mL)
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with additional EtOAc (three times)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum
  12. customThe residue was purified with flash column chromatography on silica gel eluting with 7:3/Hex

Sources & evidence

ORD record
ord-a2156f16473f4ed7894cb939404d9ed9
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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