Sodium Hydroxide → 2-(2-Chloropyridin-4-yl)-2,4-diazabicyclo[3.1.0]hexan-3-one

HRID 572422Notes

Reaction equation

HRID 572422 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]3[CH:11]([CH2:12]3)[N:10](C(OCC3C=CC=CC=3)=O)[C:9]2=[O:24])[CH:5]=[CH:4][N:3]=1.[OH-].[Na+]>Cl>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:9](=[O:24])[NH:10][CH:11]3[CH:13]2[CH2:12]3)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86729664Benzyl 4-(2-chloropyridin-4-yl)-3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate

Product 1

HCID 867296652-(2-Chloropyridin-4-yl)-2,4-diazabicyclo[3.1.0]hexan-3-oneYield 83%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of benzyl 4-(2-chloropyridin-4-yl)-3-oxo-2,4-diazabicyclo-[3.1.0]hexane-2-carboxylate (I-30b: 20.0 mg, 0.058 mmol) in 3.0 mL of 6N HCl was heated to 100° C. for 1 hour. The resulting mixture was basified with 1N NaOH. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was concentrated and washed with hexane to afford 10 mg of the product (83% yield).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. concentrationThe organic layer was concentrated
  4. washwashed with hexane

Sources & evidence

ORD record
ord-6c8dc0decbcd4ca8b84e043e6063eb9d
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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