Hydrochloric Acid → 8-(1R,5R)-3,6-Diaza-bicyclo[3.2.0]hept-3-yl-3-(3-fluoro-benzenesulfonyl)-quinoline hydrochloride

HRID 2092204Notes

Reaction equation

HRID 2092204 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[N:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[N:21]2[CH2:27][C@H:26]3[C@H:23]([CH2:24][N:25]3C(OC(C)(C)C)=O)[CH2:22]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[ClH:35]>C(O)C.C(O)(C)C>[ClH:35].[C@H:23]12[CH2:24][NH:25][C@H:26]1[CH2:27][N:21]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]3[C:14]=1[N:13]=[CH:12][C:11]([S:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)(=[O:10])=[O:9])=[CH:20]3)[CH2:22]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68728715(1S,5R)-tert-butyl 3-(3-(3-fluorophenylsulfonyl)quinolin-8-yl)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate

Product 1

HCID 687272138-(1R,5R)-3,6-Diaza-bicyclo[3.2.0]hept-3-yl-3-(3-fluoro-benzenesulfonyl)-quinoline hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

0.150 g of (1S,5R)-tert-butyl 3-(3-(3-fluorophenylsulfonyl)quinolin-8-yl)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate from Example 27 were dissolved in 5 ml of ethanol. 5 mL 5N HCl in isopropanol was added and the mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated and the residue was dissolved in small amounts of ethanol and precipitated with addition of diethyl ether. Recrystallization from ethanol/isopropanol (2:1) yielded 0.0275 g of the product.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in small amounts of ethanol
  3. customprecipitated with addition of diethyl ether
  4. customRecrystallization from ethanol/isopropanol (2:1)

Sources & evidence

ORD record
ord-808ab1efa7194fc89b4d0326addcea85
Source dataset
uspto-grants-2013_05
Patent number
US08440694B2

Reaction notes

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