Acetonitrile → Methyl 6-(2-chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoate

HRID 2357752ノート

反応式

HRID 2357752 の反応式
[NH2:1][S:2]([C:5]1[C:6]([Cl:26])=[CH:7][C:8]([NH:19][CH2:20][C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)=[C:9]([CH:18]=1)[C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11])(=[O:4])=[O:3].[CH3:27][O:28][C:29](=[O:39])[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37]Cl)=[O:35].C1CN2C(=NCCC2)C1.C(#N)C>ClCCl>[Cl:26][C:6]1[CH:7]=[C:8]([NH:19][CH2:20][C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)[C:9]([C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:15])[Cl:16])=[O:11])=[CH:18][C:5]=1[S:2]([NH:1][CH2:37][O:36][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][C:29]([O:28][CH3:27])=[O:39])(=[O:3])=[O:4]

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 19611278Chloromethyl 6-methoxy-6-oxohexanoateHCID 593891212,2,2-Trichloroethyl 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoate

生成物 1

HCID 68453359Methyl 6-(2-chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2,2,2-trichloroethyl 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoate (0.060 mole), chloromethyl 6-methoxy-6-oxohexanoate (0.060 mole), DBN (1,5-diazabicyclo[4.3.0]non-5-ene, Aldrich) (0.060 mole) and dry acetonitrile (100 mL) is stirred at ambient temperature for 10 hours. The reaction mixture is diluted with dichloromethane (200 mL) and extracted with sodium bicarbonate solution, washed with water, and then with a saturated sodium chloride solution. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo to give crude product, which is purified by column chromatography on silica gel with hexanes/ethyl acetate as eluent. The fractions that contain pure product may be combined and spin evaporated in vacuo to give methyl 6-(2-chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoate.

後処理

  1. extractionextracted with sodium bicarbonate solution
  2. washwashed with water
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give crude product, which
  7. customis purified by column chromatography on silica gel with hexanes/ethyl acetate as eluent
  8. customspin evaporated in vacuo

出典と根拠

ORDレコード
ord-b1e67845653743faa1f8e0ef00f309fd
出典データセット
uspto-grants-2010_07
特許番号
US07763612B2

反応ノート

読み込み中…