Hydrochloric Acid → HCID 76831217, compound

HRID 1186172Notes

Reaction equation

HRID 1186172 reaction equation
C(=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:30])=[C:19]([C:21]23[CH2:28][CH:27]2[CH2:26][O:25][CH2:24][C:23](=[S:29])[NH:22]3)[CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:30])=[C:19]([C:21]23[CH2:28][CH:27]2[CH2:26][O:25][CH2:24][C:23](=[S:29])[NH:22]3)[CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 76831279HCID 76831279, compound

Product 1

HCID 76831217HCID 76831217, compoundYield 255%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Crude (1SR,7RS)-1-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-oxa-2-aza-bicyclo[5.1.0]octane-3-thione (intermediate B12A) (600 mg, 1.15 mmol) was dissolved in dioxane (15 ml) and 1 M HCl (1.44 ml, 1.44 mmol) was added at 23° C. After 30 min of stirring, the reaction mixture was poured on sat. NaHCO3-solution and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated to give a dark green oil (740 mg), which was purified by silica gel column chromatography with dichloromethane/ethyl acetate to give the title compound as a light yellow solid (175 mg, 60%). MS (ISP): m/z=253.2 [(M+H)+].

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-4e21d595d5594d0ab0171c6238b418e2
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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