Hydrochloric Acid → HCID 57200673, compound

HRID 374555Notes

Reaction equation

HRID 374555 reaction equation
[Cl:1][C:2]1[C:3]([N:20]2[CH2:28][C@@H:27]3[C@@H:22]([CH2:23][CH2:24][CH2:25][NH:26]3)[CH2:21]2)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].C[Si](NC(=O)C(F)(F)F)(C)C.Cl[CH2:41][C:42]1[CH2:49][S:48][C@H:47]2[N:44]([C:45](=[O:60])[C@H:46]2[NH:50][C:51](=[O:59])[CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:43]=1[C:61]([O:63][CH:64]([C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)=[O:62].[Na+].[I-].Cl>ClCCl.CC(C)=O.O>[CH:64]([O:63][C:61]([C:43]1[N:44]2[C@H:47]([S:48][CH2:49][C:42]=1[CH2:41][N:26]1[CH2:25][CH2:24][CH2:23][C@@H:22]3[C@H:27]1[CH2:28][N:20]([C:3]1[C:2]([Cl:1])=[C:11]4[C:6]([C:7](=[O:18])[C:8]([C:15]([OH:17])=[O:16])=[CH:9][N:10]4[CH:12]4[CH2:14][CH2:13]4)=[CH:5][C:4]=1[F:19])[CH2:21]3)[C@H:46]([NH:50][C:51](=[O:59])[CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)[C:45]2=[O:60])=[O:62])([C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 119375BAY-Y-3118 free baseHCID 555527Acetamide, 2,2,2-trifluoro-N-(trimethylsilyl)-HCID 11145881HCID 11145881, compound

Product 1

HCID 57200673HCID 57200673, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Under an N2 atmosphere, 160 mg (0.4 mmol) of 8-chloro-1-cyclopropyl-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]non-8-yl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are suspended in 2.25 ml of dichloromethane. 283 μl (1.6 mmol) of trimethylsilyltrifluoroacetamide are added and the mixture is stirred at room temperature for 20 minutes; 0.5 g of 3 Å molecular sieves is then added, and the mixture is stirred at room temperature for one hour, and the solution is evaporated to dryness. Subsequently, a solution of 151 mg (0.283 mmol) of benzhydryl [6R,7R]-3-chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate in 2.25 ml of acetone is added. After addition of 46.6 mg (0.367 mmol) of NaI, the mixture is stirred overnight (20 hours), poured into water, adjusted to pH=4 with 1N HCl, and extracted 3× with ethyl acetate. The organic phase is washed with water, dried over MgSO4 and evaporated to dryness. 96 mg (0.106 mmol) (38% of theory) of the title product are obtained by chromatography on silica gel using CH2Cl2 /CH3OH (30:1).

Workup

  1. addition0.5 g of 3 Å molecular sieves is then added
  2. stirringthe mixture is stirred at room temperature for one hour
  3. customthe solution is evaporated to dryness
  4. stirringthe mixture is stirred overnight (20 hours)
  5. extractionextracted 3× with ethyl acetate
  6. washThe organic phase is washed with water
  7. dry with materialdried over MgSO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-ef11097c9c1840be84b562303c9d5969
Source dataset
uspto-grants-1996_01
Patent number
US05480879

Reaction notes

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