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

HRID 1428798노트

반응식

HRID 1428798 반응식
[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]

참가 물질

5

반응물 2

HCID 71019413Ethyl 2-[4-(aminomethyl)phenyl]propanoateHCID 178482963HCID 178482963, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0b88f19b5175482ba1ff2042b21897eb
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

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