Isopropenyl chloroformate → HCID 89611464, compound

HRID 1257168Notes

Reaction equation

HRID 1257168 reaction equation
[NH2:1][C:2]1[C:3]([F:23])=[CH:4][C:5]([CH3:22])=[C:6]([C:8]2[C:9](=[O:21])[N:10]([CH2:19][CH3:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([Cl:18])[CH:12]=3)[CH:7]=1.C([O-])(O)=O.[Na+].Cl[C:30]([O:32][C:33]([CH3:35])=[CH2:34])=[O:31]>CCOC(C)=O>[Cl:18][C:13]1[CH:12]=[C:11]2[C:16]([CH:17]=[C:8]([C:6]3[C:5]([CH3:22])=[CH:4][C:3]([F:23])=[C:2]([NH:1][C:30](=[O:31])[O:32][C:33]([CH3:35])=[CH2:34])[CH:7]=3)[C:9](=[O:21])[N:10]2[CH2:19][CH3:20])=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 93846Isopropenyl chloroformateHCID 516892Sodium BicarbonateHCID 87666922HCID 87666922, compound

Product 1

HCID 89611464HCID 89611464, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of Example A6 (0.161 g, 0.485 mmol) in EtOAc (2.5 mL) was treated with satd. NaHCO3 (2.5 mL) followed by isopropenyl chloroformate (0.080 mL, 0.728 mmol) and the bi-phasic mixture stirred vigorously at RT for 2 h. The layers were separated, the organic layer washed with brine dried over MgSO4 and concentrated to dryness to afford prop-1-en-2-yl (5-(7-chloro-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl)carbamate (100% yield assumed). MS (ESI) m/z: 416.1 [M+H]+.

Workup

  1. customThe layers were separated
  2. washthe organic layer washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d5ecf5e475ff466293ccadce53f77cbd
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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