Phenylacetaldehyde → 2-Phenyl-1-(thiophene-2-sulfonylamino)-ethyl-phosphonic Acid Diethyl Ester

HRID 993095

반응식

HRID 993095 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH2:9])(=[O:8])=[O:7].[P:10]([O-:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13].[C:18]1([CH2:24][CH:25]=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(=O)C>[CH2:12]([O:11][P:10]([CH:25]([NH:9][S:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:8])=[O:7])[CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])[O:14][CH2:15][CH3:16])[CH3:13]

참가 물질

5

반응물 3

HCID 998PhenylacetaldehydeHCID 728812-ThiophenesulfonamideHCID 3780918Diethylphosphite

생성물 1

HCID 228909322-Phenyl-1-(thiophene-2-sulfonylamino)-ethyl-phosphonic Acid Diethyl Ester수율 349.4%

시약·촉매·용매 1

HCID 6367Acetyl chloride용매

반응 조건

온도
0 °C

실험 절차

To a suspension of sulfonamide (vi) (500 mg; 0.31 mmol) in acetyl chloride (5 mL) was slowly added diethyl phosphite (400 μL; 0.31 mmol). The reaction was cooled to 0° C. and then phenylacetaldehyde (450 μL; 0.39 mmol) was added dropwise. The reaction was gradually warmed to ambient temperature and after 6 hrs the homogeneous solution was concentrated. The residue was diluted with dichloromethane (25 mL) then washed successively with water (10 mL), saturated sodium bicarbonate (10 mL) and brine (10 mL). The combined organic extracts wre dried (MgSO4), evaporated and initially purified by flash chromatography (ethyl acetate-hexanes; 3:2). A second purification by flash chromatography (acetone-hexanes; 3:7) yielded diethyl phosphonate (xii) (437 mg, 35%) as a colorless solid; 1H NMR (400 MHz, CDCl3) δH 1.22 (t, J=7 Hz, 3H, OCH2CH3), 1.26 (t, J=7 Hz, 3H, OCH2CH3), 2.89 (dt, J=8, 14 Hz, 1H, CHPh), 3.12 (dt, J=6, 14 Hz, 1H. CHPh), 3.96-4.23 (m, 5H, NCHP and OCH2CH3), 6.38 (dd, J=2, 9.5 Hz, 1H, NH), 6.92-6.93 (m, 1H, Ar—H), 7.12-7.20 (m, 5H, Ar—H), 7.33-7.34 (m, 1H, Ar—H), 7.43-7.45 (m, 1H, Ar—H).

후처리

  1. temperatureThe reaction was gradually warmed to ambient temperature and after 6 hrs the homogeneous solution
  2. concentrationwas concentrated
  3. additionThe residue was diluted with dichloromethane (25 mL)
  4. washthen washed successively with water (10 mL), saturated sodium bicarbonate (10 mL) and brine (10 mL)
  5. dry with materialThe combined organic extracts wre dried (MgSO4)
  6. customevaporated
  7. custominitially purified by flash chromatography (ethyl acetate-hexanes; 3:2)
  8. customA second purification by flash chromatography (acetone-hexanes; 3:7)

출처 및 근거

ORD 기록
ord-39b4de1fe3a94fe8b5b69f418ecfab41
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06472406B1

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