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

HRID 1027413ノート

反応式

HRID 1027413 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fc11527274d645edabde4dbb35428fd9
出典データセット
uspto-grants-2014_05
特許番号
US08735385B2

反応ノート

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