Hydrochloric Acid → HCID 76470919, compound

HRID 2276721Notes

Reaction equation

HRID 2276721 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:10]23[CH:15]([CH:16]=[N:17][O:18][CH2:19][CH3:20])[CH:14]2[CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]3)[CH:6]=[CH:7][C:8]=1[Cl:9].CCCCCC>C(Cl)Cl>[ClH:2].[CH2:19]([O:18][N:17]=[CH:16][CH:15]1[C:10]2([C:5]3[CH:6]=[CH:7][C:8]([Cl:9])=[C:3]([Cl:2])[CH:4]=3)[CH:14]1[CH2:13][NH:12][CH2:11]2)[CH3:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 86697413HCID 86697413, compound

Product 2

HCID 313Hydrochloric AcidHCID 76470919HCID 76470919, compoundYield 153.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl (g) was bubbled through a solution of tert-butyl 1-(3,4-dichlorophenyl)-6-((ethoxyimino)methyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (70 mg, 0.17 mmol) obtained in step-2 of example 6 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 1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane-6-carbaldehyde O-ethyl oxime (39 mg, 95%) 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-fc6e2fc1f7f2404098e6c55f6229dc7b
Source dataset
uspto-grants-2015_09
Patent number
US09133116B2

Reaction notes

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