Benzyl chloroformate → HCID 124008951, compound

HRID 590551Notes

Reaction equation

HRID 590551 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]([CH3:24])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:13]1.C([O-])(O)=O.[Na+].[C:30](Cl)([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>C1COCC1.[Pd]>[CH2:33]([O:32][C:30](=[O:31])[NH:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([N:12]2[CH2:17][CH2:16][Si:15]([CH3:24])([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)=[C:4]([F:11])[CH:5]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 89501592HCID 89501592, compound

Product 1

HCID 124008951HCID 124008951, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 23938PalladiumSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 9b (1.96 g, 7.59 mmol) in THF, Pd/C is added for hydrogenation under a pressure of 35 psi in a par hydrogenator. The reaction mixture was filtered through celite. To the filtrate, saturated NaHCO3 (1.90 g, 22.77 mmol) and CBzCl (1.3 mL, 9.10 mmol) were added and stirred at 25° C. for 5 h. The solvent is removed, 10 mL water is 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 10b as a viscous liquid (1.80 g) in 71% yield.

Workup

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

Sources & evidence

ORD record
ord-a4a29d9f5e0c444a9027b3d2ea745267
Source dataset
uspto-grants-2016_01
Patent number
US09233989B2

Reaction notes

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