Hydrochloric Acid → HCID 19425878、化合物

HRID 742294ノート

反応式

HRID 742294 の反応式
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:13])=[O:12])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[Li]CCCC.[B:23]([O:32]C(C)C)([O:28]C(C)C)[O:24]C(C)C.Cl>C1COCC1>[C:14]([S:11]([NH:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:1][CH2:2][CH3:3])=[CH:9][C:8]=1[O:24][B:23]([OH:32])[OH:28])(=[O:13])=[O:12])([CH3:16])([CH3:15])[CH3:17]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 194258794-n-Propylphenyl-t-butylsulfonamideHCID 178418339Butyllithium

生成物 1

HCID 19425878HCID 19425878、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-n-propylphenyl-t-butylsulfonamide (2.85 g, 11.2 mmoL) in anhydrous THF (20 mL) cooled to -40° C. under N2 was added 2.5M n-BuLi solution (11.2 mL, 2.5 equiv). The mixture was warmed to rt and stirred for 2 h. To the mixture, containing the bright red dianion at 0° C., was added B(OiPr)3 (3.9 mL, 1.5 equiv). The next day 2N HCl (3 mL) was added and the mixtue was stirred for 1 h. The solvent was removed under reduced pressure and the residue was extracted With EtOAc. The organic was washed with 2N HCl, H2O and brine. The organic was dried over anhydrous MgSO4 and concentrated in vacuo to afford the titled compound. Rf=0.5 (1:1 EtOAc/Hex). The crude material was used in subsequent steps without further purification.

後処理

  1. additionTo the mixture, containing the bright red dianion at 0° C.
  2. stirringthe mixtue was stirred for 1 h
  3. customThe solvent was removed under reduced pressure
  4. extractionthe residue was extracted With EtOAc
  5. washThe organic was washed with 2N HCl, H2O and brine
  6. dry with materialThe organic was dried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2fd377b54efe4f1f923281eb6116e7f0
出典データセット
uspto-grants-1996_09
特許番号
US05554625

反応ノート

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