Dichloromethane → HCID 54341699, 화합물

HRID 361458노트

반응식

HRID 361458 반응식
[CH2:1]([O:5][C:6]([N:8]([C:26]1[C:31]([O:32][CH3:33])=[N:30][C:29]([CH3:34])=[CH:28][N:27]=1)[S:9]([C:12]1[C:13]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=2)=[N:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])=[O:10])=[O:7])[CH:2]([CH3:4])[CH3:3].[Br-].[C:36]([CH2:39][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:38])=[O:37].[OH-].[Na+].[CH2:61](Cl)Cl>O>[CH2:1]([O:5][C:6]([N:8]([C:26]1[C:31]([O:32][CH3:33])=[N:30][C:29]([CH3:34])=[CH:28][N:27]=1)[S:9]([C:12]1[C:13]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH:39][C:36]([O:38][CH3:61])=[O:37])=[CH:20][CH:19]=2)=[N:14][CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:11])=[O:7])[CH:2]([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 21186316N-isobutoxycarbonyl-2-(4-formylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamideHCID 21186329Carboxymethyl triphenylphosphonium bromide

생성물 1

HCID 54341699HCID 54341699, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

N-isobutoxycarbonyl-2-(4-formylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (500 mg) was added to carboxymethyl triphenylphosphonium bromide (429 mg) in a mixture of saturated aqueous sodium hydroxide (1.25 ml) and methylene chloride (4 ml) and stirred vigorously at ambient temperature for 1.5 hours. Water (20 ml) was added and the mixture extracted with dichloromethane (2×20 ml). The combined organic extracts were, washed with water (5 ml), dried (MgSO4) and evaporated. The residue was purified by chromatography on a Mega Bond Elut column, eluting with a gradient of 0-30% ethyl acetate in hexane. Fractions containing the product were combined, evaporated and the residue was triturated with diethyl ether/isohexane (1:1 v/v) and filtered to give N-isobutoxycarbonyl-2-[4-(2-[methoxycarbonyl]vinyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (366 mg), m.p 155°-156° C.; 1H NMR (CDCl3): 0.65 (d, 6 H), 1.7 (septet, 1 H), 2.5 (s, 3 H), 3.82 (s, 3 H), 3.85 (d, 2 H), 3.98 (s, 3 H), 6.48 (d, 1 H), 7.4-7.8 (m , 7 H), 7.9 (s, 1 H), 8.86 (dd, 1 H), 8.98 (dd, 1 H).

후처리

  1. extractionthe mixture extracted with dichloromethane (2×20 ml)
  2. washwashed with water (5 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography on a Mega Bond Elut column
  6. washeluting with a gradient of 0-30% ethyl acetate in hexane
  7. additionFractions containing the product
  8. customevaporated
  9. customthe residue was triturated with diethyl ether/isohexane (1:1 v/v)
  10. filtrationfiltered

출처 및 근거

ORD 기록
ord-15616f2e13284c47bd981b1f37988e7a
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866568

반응 노트

불러오는 중…