Ethyl Acetate → HCID 178522213, compound

HRID 2283471Notes

Reaction equation

HRID 2283471 reaction equation
[NH2:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:9](Cl)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C>C(Cl)Cl>[OH:8][C:3]1[C:2]([NH:1][C:9](=[O:10])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 178418824HCID 178418824, compound

Product 1

HCID 178522213HCID 178522213, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-aminopyridin-2-ol (8.05 g, 73.0 mmol) in DCM (20 mL) was added CbzCl (13.2 mL, 93.0 mmol) and Na2CO3 (18.0 g, 170 mmol). The mixture was stirred at room temperature overnight. Ethyl acetate (500 mL) was added and the mixture was washed with NaHCO3 (50 mL). The organic phase was dried over MgSO4, filtered and concentrated. The crude product was purified by combi-flash (ISCO, 40 g silica, MeOH/DCM from 3% to 5%, UV254) to afford benzyl (2-hydroxypyridin-3-yl)carbamate (16.2 g, 90% yield): MS (ES) m/z 245 (M+H).

Workup

  1. washthe mixture was washed with NaHCO3 (50 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by combi-flash (ISCO, 40 g silica, MeOH/DCM from 3% to 5%, UV254)

Sources & evidence

ORD record
ord-1247cc8a58254fa085f87a4a0a62fe45
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

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