Sodium Hydroxide → HCID 178520552, compound

HRID 1480454Notes

Reaction equation

HRID 1480454 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]([NH:9][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][C:14]1[N:15]=[N:16][NH:17][CH:18]=1)[CH2:2]2.[C:20](Cl)(=[O:31])[O:21][CH2:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=1.[OH-].[Na+]>C(Cl)Cl>[NH:17]1[CH:18]=[C:14]([CH2:13][CH2:12][CH2:11][C:10]([NH:9][CH:3]2[CH2:2][CH:1]3[N:8]([C:20]([O:21][CH2:22][C:23]4[CH:24]=[C:25]([Cl:30])[CH:26]=[C:27]([Cl:29])[CH:28]=4)=[O:31])[CH:5]([CH2:6][CH2:7]3)[CH2:4]2)=[O:19])[N:15]=[N:16]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 133055323,5-Dichlorobenzyl ChloroformateHCID 178520551HCID 178520551, compound

Product 1

HCID 178520552HCID 178520552, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction mixture comprising of N-(8-azabicyclo[3.2.1]octan-3-yl)-4-(1H-1,2,3-triazol-4-yl)butanamide (294 mg, 1.116 mmol), 3,5-dichlorobenzyl carbonochloridate (267 mg, 1.116 mmol) and sodium hydroxide (5.58 ml, 112 mmol) in DCM (3.7 ml) was stirred at room temperature for 18 hours. The reaction mixture was separated and the organic portion was dried over MgSO4, filtered and concentrated under reduced pressure. Further purification was carried out using preparative LC-MS and the resulting product fractions were concentrated under reduced pressure to give aqueous solutions which were extracted with ethyl acetate. The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound.

Workup

  1. customThe reaction mixture was separated
  2. dry with materialthe organic portion was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customFurther purification
  6. concentrationthe resulting product fractions were concentrated under reduced pressure
  7. customto give aqueous solutions which
  8. extractionwere extracted with ethyl acetate
  9. dry with materialThe organic extracts were dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4508f2ef1b66421093207d55c25b443f
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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