Benzyl chloroformate → {4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-2-fluoro-phenyl}-carbamic acid benzyl ester

HRID 1027413Notes

Reaction equation

HRID 1027413 reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([F:20])[CH:14]=2)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[C:23](Cl)([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:26]([O:25][C:23](=[O:24])[NH:19][C:16]1[CH:17]=[CH:18][C:13]([CH:10]2[CH2:11][CH2:12][CH:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:22])[CH3:21])[CH2:8][CH2:9]2)=[CH:14][C:15]=1[F:20])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 674792044-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-2-fluoro-phenylamine

Product 1

HCID 67479416{4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-2-fluoro-phenyl}-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-2-fluoro-phenylamine (0.85 g, 2.4 mmol) was dissolved in DCM (20 mL). To this solution was transferred a solution of CbzCl (560 mg, 3.28 mmol, 1.3 equiv.) in 5 mL of DCM, followed by addition of powder anhydrous K2CO3 (0.99 g, 7.2 mmol, 3 equiv.). The reaction mixture was stirred at 0° C. to rt. overnight. The reaction was quenched by dilution with DCM (10 mL), followed by addition of NaHCO3 aq. (5 mL). The two layers were separated and the aqueous layer was extracted with DCM (2×5 mL). The combined extracts were washed with NaHCO3 aq. (5 mL), brine (5 mL) and dried (K2CO3). The solution was filtered and the filtrate was concentrated in vacuo to obtain the title compound.

Workup

  1. customovernight
  2. customThe reaction was quenched by dilution with DCM (10 mL)
  3. additionfollowed by addition of NaHCO3 aq. (5 mL)
  4. customThe two layers were separated
  5. extractionthe aqueous layer was extracted with DCM (2×5 mL)
  6. washThe combined extracts were washed with NaHCO3 aq. (5 mL), brine (5 mL)
  7. dry with materialdried (K2CO3)
  8. filtrationThe solution was filtered
  9. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fc11527274d645edabde4dbb35428fd9
Source dataset
uspto-grants-2014_05
Patent number
US08735385B2

Reaction notes

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