Formaldehyde → Chloromethyl 4-(3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoate

HRID 2357742ノート

反応式

HRID 2357742 の反応式
[NH2:1][S:2]([C:5]1[C:6]([Cl:32])=[CH:7][C:8]([NH:25][CH2:26][C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)=[C:9]([CH:24]=1)[C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:23])[CH2:18][CH2:19][C:20](Cl)=[O:21])=[O:11])(=[O:4])=[O:3].C=[O:34].Cl[CH2:36][Cl:37]>>[NH2:1][S:2]([C:5]1[C:6]([Cl:32])=[CH:7][C:8]([NH:25][CH2:26][C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)=[C:9]([CH:24]=1)[C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:23])[CH2:18][CH2:19][C:20]([O:34][CH2:36][Cl:37])=[O:21])=[O:11])(=[O:3])=[O:4]

参加物

4

反応物 3

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 866134344-(3-(5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoyl chloride

生成物 1

HCID 68457545Chloromethyl 4-(3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoate

反応条件

温度
90 °C

実験手順

A mixture of 4-(3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoyl chloride (813) (0.040 mole) and paraformaldehyde (0.040 mole) is heated in a sealed vessel at 90° C. for 3 hours. The reaction is cooled, and the solids are dissolved in dichloromethane. The solution is washed with 5% aqueous sodium bicarbonate, 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 may be 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 chloromethyl 4-(3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoate (815). See eg., Bodor, et al., J. Med. Chem., 23, 469 (1980), and Ulich, et al., J. Am. Chem. Soc., (1921) 43: 660.

後処理

  1. temperatureThe reaction is cooled
  2. washThe solution is washed with 5% aqueous sodium bicarbonate, 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. custommay be 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-f4d17efbb9f24fee8dede1ab8574be29
出典データセット
uspto-grants-2010_07
特許番号
US07763612B2

反応ノート

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