Hydrochloric Acid → HCID 86678182, compound

HRID 2366563Notes

Reaction equation

HRID 2366563 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([F:22])[CH:18]=3)[N:13]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]=2[CH2:11][CH2:10]1)=O)(C)(C)C.[ClH:29].O1CCOCC1>C(Cl)Cl>[ClH:29].[NH2:8][C@@H:9]1[CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([F:22])[CH:18]=3)[N:13]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]=2[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86678184HCID 86678184, compound

Product 1

HCID 86678182HCID 86678182, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of (S)-ethyl 2-(3-((tert-butoxycarbonyl)amino)-6-fluoro-3,4-dihydro-1H-carbazol-9(2H)-yl)acetate (8.2 g, 0.021 mol) in dry DCM (50 ml) was added dropwise 4N HCl in dioxane (52.5 ml, 0.21 mol). The resulting reaction mixture was stirred at 0° C. for 2 h and then at rt for 5 h. The reaction mixture was concentrated in vacuo and the resulting solid was dissolved in EtOH (70 ml) and was added at 0° C. 3N HCl in EA (7 ml). The reaction mixture was stirred at reflux overnight. After cooling to rt, the reaction mixture was concentrated in vacuo to afford the title compound as a beige powder.

Workup

  1. customThe resulting reaction mixture
  2. waitat rt for 5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe resulting solid was dissolved in EtOH (70 ml)
  5. additionwas added at 0° C
  6. stirringThe reaction mixture was stirred
  7. temperatureat reflux overnight
  8. temperatureAfter cooling to rt
  9. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-588afa85987143aaadfa6b2c14dcde03
Source dataset
uspto-grants-2014_04
Patent number
US08697869B2

Reaction notes

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