Hydrochloric Acid → HCID 86697405, compound

HRID 2276714Notes

Reaction equation

HRID 2276714 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:10](=[N:24][O:25][CH2:26][CH3:27])[CH:11]2[CH:16]3[CH:12]2[CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15]3)[CH:6]=[CH:7][C:8]=1[Cl:9].CCCCCC>C(Cl)Cl>[ClH:2].[CH2:26]([O:25][N:24]=[C:10]([CH:11]1[CH:16]2[CH:12]1[CH2:13][NH:14][CH2:15]2)[C:5]1[CH:6]=[CH:7][C:8]([Cl:9])=[C:3]([Cl:2])[CH:4]=1)[CH3:27]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 86697403HCID 86697403, compound

Product 2

HCID 313Hydrochloric AcidHCID 86697405HCID 86697405, compoundYield 200.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl (g) was bubbled through a solution of tert-butyl 6-((3,4-dichlorophenyl)(ethoxyimino)methyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (100 mg, 0.25 mmol) obtained in step-2 of example 1 in dry DCM (5 mL). After the completion of the reaction as confirmed by TLC, the reaction mixture was purged with excess of nitrogen. The solvent was removed in vacuo to afford a gummy solid which was titurated with hexane to afford hydrochloric acid salt of 3-azabicyclo[3.1.0]hexan-6-yl(3,4-dichlorophenyl)methanone O-ethyl oxime (75 mg, 86%) as a white solid as a mixture of isomers.

Workup

  1. customAfter the completion of the reaction
  2. customthe reaction mixture was purged with excess of nitrogen
  3. customThe solvent was removed in vacuo
  4. customto afford a gummy solid which

Sources & evidence

ORD record
ord-c4a6eafbc9f44a228077b157d184a655
Source dataset
uspto-grants-2015_09
Patent number
US09133116B2

Reaction notes

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