Ethyl 2-[4-(aminomethyl)phenyl]propanoate → ethyl 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoate

HRID 1428798ノート

反応式

HRID 1428798 の反応式
[C:1]([O:5][C:6]([NH:8][S:9](N1C=CC(=[N+](C)C)C=C1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:25][CH:24]=1>ClCCl.O>[C:1]([O:5][C:6]([NH:8][S:9]([NH:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([CH:29]([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:27][CH:28]=1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 71019413Ethyl 2-[4-(aminomethyl)phenyl]propanoateHCID 178482963HCID 178482963、化合物

生成物 1

HCID 86680233ethyl 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoate収率 51%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

N-(1-(tert-butoxycarbonyl)sulfamoyl)pyridine-4(1H)-ylidene)-N-methylmethanaminium (A) (5.81 g, 19.32 mmol) was added to a suspension of ethyl 2-(4-(aminomethyl)phenyl)propanoate (4.0 g, 19.32 mmol) in dichloromethane (40 mL) at room temperature and stirred for 16 h. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (2×75 mL). Combined organic layer was washed with water (50 mL), brine (50 mL), dried over sodium sulfate and concentrated to get crude compound, which was purified by column chromatography (silica gel; 100-200 mesh). The product eluted with 20% ethyl acetate in pet ether to yielded ethyl 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoate (3.8 g, 51%) as pale yellow solid.

後処理

  1. extractionextracted with ethyl acetate (2×75 mL)
  2. washCombined organic layer was washed with water (50 mL), brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto get crude compound, which
  6. customwas purified by column chromatography (silica gel; 100-200 mesh)
  7. washThe product eluted with 20% ethyl acetate in pet ether

出典と根拠

ORDレコード
ord-0b88f19b5175482ba1ff2042b21897eb
出典データセット
uspto-grants-2015_01
特許番号
US08937092B2

反応ノート

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