Benzyl chloroformate → HCID 89500539, compound

HRID 590541Notes

Reaction equation

HRID 590541 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][Si:14]([CH3:18])([CH3:17])[CH2:13][CH2:12]1.C([O-])(O)=O.[Na+].[C:24](Cl)([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>O1CCCC1>[CH3:17][Si:14]1([CH3:18])[CH2:15][CH2:16][N:11]([C:3]2[CH:4]=[CH:5][C:6]([NH:8][C:24](=[O:25])[O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:7][C:2]=2[F:1])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 89501539HCID 89501539, compound

Product 1

HCID 89500539HCID 89500539, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 9 (610 mg, 2.28 mmol) in Tetrahydrofuran (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 (420 mg, 5.01 mmol), CBzCl (427 mg, 2.5 mmol) are 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 10 as a viscous liquid (690 mg) in 82% yield.

Workup

  1. filtrationThe reaction mixture is 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-d48aa9821264410e9101000ae07c60f2
Source dataset
uspto-grants-2016_01
Patent number
US09233989B2

Reaction notes

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