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Diisopropylethylamine → HCID 67908631, 화합물

HRID 467368
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HRID 467368 반응식
C(N(CC)C(C)C)(C)C.Cl[CH2:11][C:12]1[CH2:13][S:14][C@@H:15]2[C@H:35]([NH:36][C:37](=[O:45])[CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:34](=[O:46])[N:16]2[C:17]=1[C:18]([O:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].[SH:47][C:48]1[CH2:52][O:51][C:50](=[O:53])[CH:49]=1>ClCCl>[O:53]=[C:50]1[CH:49]=[C:48]([S:47][CH2:11][C:12]2[CH2:13][S:14][C@@H:15]3[C@H:35]([NH:36][C:37](=[O:45])[CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:34](=[O:46])[N:16]3[C:17]=2[C:18]([O:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:52][O:51]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 11145881HCID 11145881, 화합물HCID 198129894-Sulfanylfuran-2(5H)-one

생성물 1

HCID 67908631HCID 67908631, 화합물수율 89.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N,N-Diisopropylethylamine (0.52 ml) was added to a stirred solution of diphenylmethyl 3-chloromethyl-7β-phenylacetamidoceph-3-em-4-carboxylate (1.59 g) and 4-mercapto-2(5H)-furanone (400 mg) in dichloromethane (30 ml). The mixture was stirred at room temperature for 2 hours and then washed successively with aqueous citric acid solution, water, sodium bicarbonate solution, water and brine. The solution was dried over magnesium sulphate and evaporated. The title compound (1.64 g) was isolated by column chromatography of the residue using gradient elution (Kieselgel, 1:1 going to 3:7 hexane:ethyl acetate), m.p. 178°-180° C. from ethyl acetate/hexane (Found: C, 64.89; H, 4.61; N, 4.57; S, 10.30: C33H28N2O6S2 requires; C, 64.69; H, 4.61; N, 4.57; S, 10.47). υmax (CHCl3) 3400, 1780, 1745, and 1680 cm-1. δH (CDCl3) 3.36 (1H, d, J 18.3Hz), 3.57 (1H, d, J 18.3Hz), 3.62 (1H, d, J 16.2Hz), 3.70 (1H, d, J 16.2Hz), 3.86 (1H, d, J 12.5Hz), 4.01 (1H, d, J 12.5Hz), 4.71 (2H, s), 4.98 (1H, d, J 4.8Hz), 5.64 (1H, s), 5.88 (1H, dd, J 4.8 and 9.0Hz), 6.06 (1H, d, J 9.0Hz), 6.95 (1H, s), 7.2-7.4 (15H, m).

후처리

  1. washwashed successively with aqueous citric acid solution, water, sodium bicarbonate solution, water and brine
  2. dry with materialThe solution was dried over magnesium sulphate
  3. customevaporated

출처 및 근거

ORD 기록
ord-3f366480f1f04091a8f517cf38ab1157
출처 데이터셋
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05158946

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