Sodium Methoxide → HCID 70074918, 화합물

HRID 1034172노트

반응식

HRID 1034172 반응식
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=[C:16]([N+:20]([O-:22])=[O:21])[C:17](=O)[CH3:18])(=[O:8])=[O:7].Cl.[CH3:24][O:25][C:26](=[O:31])[CH2:27][C:28](=[NH:30])[NH2:29].C[O-].[Na+]>CO>[CH3:24][O:25][C:26]([C:27]1[CH:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:6]([CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])(=[O:8])=[O:7])[C:16]([N+:20]([O-:22])=[O:21])=[C:17]([CH3:18])[NH:29][C:28]=1[NH2:30])=[O:31]

참가 물질

5

반응물 3

HCID 10942334Sodium MethoxideHCID 19988776Methyl 2-Amidinoacetate HydrochlorideHCID 54506574HCID 54506574, 화합물

생성물 1

HCID 70074918HCID 70074918, 화합물수율 26.3%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a solution of 3.2 g of 4-{2-[(4-chlorobutyl)sulfonyl]phenyl}-3-nitro-3-buten-2-one in 25 ml of methanol in a 100 ml single-neck flask at 0° C. was added 1.41 g of amidino-acetic acid methyl ester hydrochloride, followed by 2.2 ml of 25% sodium methoxide in methanol. The mixture was warmed to room temperature and stirred overnight. After removal of the methanol, the residue was partitioned between water and dichloromethane. The organic layer was dried over magnesium sulfate and evaporated to give a crude product, which was purified via column chromatography on silica gel, eluting with 60:40 toluene:ethyl acetate. Recrystallization from isopropyl acetate provided 1.08 g of an orange product, m.p. 218° C. 1H-NMR (d6 -DMSO) δ 1.71-1 95(m,4H); 2.45(s,3H); 2.48-2.55(m,2H); 3.34(s,3H); 3.69(m,2H); 6.49(s,1H); 6.87(br s,2H); 7.33-7.44(m,2H); 7.56(t,1H,J=8 Hz); 7.79(d,1H,J=8 Hz); 9.51(br s,1H). Mass spectrum: 444 (M+H).

후처리

  1. customAfter removal of the methanol
  2. customthe residue was partitioned between water and dichloromethane
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated
  5. customto give a crude product, which
  6. customwas purified via column chromatography on silica gel
  7. washeluting with 60:40 toluene
  8. customRecrystallization from isopropyl acetate

출처 및 근거

ORD 기록
ord-58da145735af4164b836d4d39c9778e1
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05314887

반응 노트

불러오는 중…