Trifluoroacetic acid → N-(3-(Aminomethyl)benzyl)-3,5-dichloro-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxybenzenesulfonamide

HRID 1889679ノート

反応式

HRID 1889679 の反応式
[Cl:1][C:2]1[C:3]([OH:43])=[C:4]([S:9]([N:12]([CH2:27][C:28]2[CH:29]=[C:30]([CH:40]=[CH:41][CH:42]=2)[CH2:31][NH:32]C(=O)OC(C)(C)C)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:32][CH2:31][C:30]1[CH:29]=[C:28]([CH:42]=[CH:41][CH:40]=1)[CH2:27][N:12]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[S:9]([C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[OH:43])(=[O:11])=[O:10]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 58531334tert-Butyl 3-((3,5-dichloro-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate

生成物 1

HCID 58531533N-(3-(Aminomethyl)benzyl)-3,5-dichloro-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxybenzenesulfonamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

tert-Butyl 3-[(3,5-dichloro-N-((4′-fluorobiphenyl-4-yl)methyl]-2-hydroxyphenylsulfonamido) methyl)benzylcarbamate (1.0 g, 1.5 mmol, 1 eq) was dissolved in dry DCM, stirred for 10 minutes and cooled to 0° C. Trifluoroacetic acid (3.5 g, 309 mmol 20 eq) was added slowly at 0° C. The reaction mixture was stirred for 10 min and slowly brought to rt. After 4 h, the solvent was evaporated under reduced pressure, and ethyl acetate and 10% aq. NaHCO3 solution were added. The mixture was stirred for 10 minutes and the aqueous mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and evaporated under reduced pressure. The crude salt (0.7 g, 82%) was used immediately in the next step. 1H NMR (400 MHz, DMSO-d6) δ 3.52 (s, 2H), 4.44 (s, 2H), 4.46 (s, 2H), 6.9-6.99 (t, 2H), 7.08-7.10 (d, 2H), 7.17-7.20 (m, 4H), 7.22-7.27 (m, 2H), 7.44-7.46 (d, 2H), 7.6-7.65 (t, 2H). MS (ESI): 546.0 (M+H)+.

後処理

  1. stirringThe reaction mixture was stirred for 10 min
  2. customslowly brought to rt
  3. waitAfter 4 h
  4. customthe solvent was evaporated under reduced pressure, and ethyl acetate and 10% aq. NaHCO3 solution
  5. additionwere added
  6. stirringThe mixture was stirred for 10 minutes
  7. extractionthe aqueous mixture was extracted with ethyl acetate
  8. dry with materialThe organic layer was dried with anhydrous Na2SO4
  9. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-d1efcaa188e24c45bac9a2edd1e4b1d7
出典データセット
uspto-grants-2013_08
特許番号
US08501992B2

反応ノート

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