Benzyl chloroformate → HCID 89508658, compound

HRID 590549Notes

Reaction equation

HRID 590549 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH2:17][CH2:16][Si:15]([CH3:19])([CH3:18])[CH2:14][CH2:13]1.C([O-])(O)=O.[Na+].[C:25](Cl)([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>C1COCC1.[Pd]>[CH2:28]([O:27][C:25](=[O:26])[NH:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([N:12]2[CH2:17][CH2:16][Si:15]([CH3:19])([CH3:18])[CH2:14][CH2:13]2)=[C:4]([F:11])[CH:5]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 89501582HCID 89501582, compound

Product 1

HCID 89508658HCID 89508658, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 23938PalladiumSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 9a (1.32 g, 4.61 mmol) in THF, Pd/C is added for hydrogenation under a pressure of 35 psi in a par hydrogenator. The reaction mixture is filtered through celite. To the filtrate, saturated NaHCO3 (1.16 g, 13.84 mmol), CBzCl (1.17 g, 6.93 mmol) are added and stirred at 25° C. for 5 h. The solvent is removed, 10 mL water is then added and the aqueous layer is extracted with EtOAc. The crude mixture is then subjected to column chromatography on silica gel using hexane-DCM mixtures to afford the product 10a as a viscous liquid (1.25 g) in 69% yield.

Workup

  1. filtrationThe reaction mixture is filtered through celite
  2. customThe solvent is removed
  3. addition10 mL water is then added
  4. extractionthe aqueous layer is extracted with EtOAc

Sources & evidence

ORD record
ord-d18b5a4bc37644d1b19154686882518a
Source dataset
uspto-grants-2016_01
Patent number
US09233989B2

Reaction notes

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