Benzyl chloroformate → HCID 67350493, compound

HRID 527962Notes

Reaction equation

HRID 527962 reaction equation
[O:1]1[C:10]2[C:5](=[N:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[O:4][CH2:3][CH2:2]1.C([O-])(O)=O.[Na+].[C:17](Cl)([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>CC(C)=O.O>[CH2:20]([O:19][C:17](=[O:18])[NH:11][C:7]1[N:6]=[C:5]2[O:4][CH2:3][CH2:2][O:1][C:10]2=[CH:9][CH:8]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 15633302129421-39-2

Product 1

HCID 67350493HCID 67350493, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A solution of 2,3-dihydro-1,4-dioxino[2,3-b]pyridin-6-amine (commercial; 2.70 g) in acetone/water 1:1 (40 mL) was treated at 0° C. with 1M NaHCO3 (35 mL) and CbzCl (2.63 mL). The reaction mixture was stirred at rt for 3 h, the org. solvent was evaporated under reduced pressure and the residue was partitioned between water and ether/EA. The org layer was dried over MgSO4 and evaporated under reduced pressure, affording a beige solid (5.3 g; 100% yield).

Workup

  1. customsolvent was evaporated under reduced pressure
  2. customthe residue was partitioned between water and ether/EA
  3. dry with materialThe org layer was dried over MgSO4
  4. customevaporated under reduced pressure
  5. customaffording a beige solid (5.3 g; 100% yield)

Sources & evidence

ORD record
ord-2b6db1173e374adbbac2156c2ea69c87
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

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