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Dicyclohexylcarbodiimide → HCID 88499001, 화합물

HRID 477527
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HRID 477527 반응식
[C:1]1([C:7]([NH:20][C:21]2[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C:32]([C:34]3[O:35][CH:36]=[CH:37][CH:38]=3)=[O:33])/[C:27](O)=[O:28])[N:25]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:39]1([CH:45]([O:52][C:53]([C:55]2[N:56]3[C@H:59]([S:60][CH2:61][C:62]=2[CH2:63][S:64][C:65]2[N:70]4[N:71]=[C:72]([C:74]([O:76][CH:77]([C:84]5[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=5)[C:78]5[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=5)=[O:75])[N:73]=[C:69]4[N:68]=[C:67]([CH3:90])[CH:66]=2)[C@H:58]([NH2:91])[C:57]3=[O:92])=[O:54])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:39]1([CH:45]([O:52][C:53]([C:55]2[N:56]3[C@H:59]([S:60][CH2:61][C:62]=2[CH2:63][S:64][C:65]2[N:70]4[N:71]=[C:72]([C:74]([O:76][CH:77]([C:84]5[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=5)[C:78]5[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=5)=[O:75])[N:73]=[C:69]4[N:68]=[C:67]([CH3:90])[CH:66]=2)[C@H:58]([NH:91][C:27](=[O:28])/[C:26](/[C:24]2[N:25]=[C:21]([NH:20][C:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[S:22][CH:23]=2)=[N:30]\[O:31][C:32]([C:34]2[O:35][CH:36]=[CH:37][CH:38]=2)=[O:33])[C:57]3=[O:92])=[O:54])[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 13821813HCID 13821813, 화합물HCID 14850390HCID 14850390, 화합물

생성물 1

HCID 88499001HCID 88499001, 화합물수율 73.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-30 °C

실험 절차

The product obtained in Example 29 (3.1 g) and the product obtained in Example 15 (4.3 g) were dissolved in anhydrous dichloromethane (200 ml) with stirring, the faint yellow solution was cooled to -30° C., and a solution of dicyclohexylcarbodiimide (1.2 g) in anhydrous dichloromethane (30 ml) was dropwise added over a period of five minutes. The resulting faint yellow solution was allowed to stand at 0° C. for nine hours, the colorless crystals separated were removed by filtration, and the filtrate was washed with 50 ml of 1N aqueous citric acid, 50 ml of saturated sodium bicarbonate solution and 80 ml of saturated sodium chloride solution in that order and dried over anhydrous sodium sulfate. The dried filtrate was concentrated in vacuo, the yellow, viscous residue (6.8 g) was purified by silica gel column chromatography using ethyl acetate/n-hexane as eluent, yielding 5.3 g of the objective compound as faint yellow crystals.

후처리

  1. customthe colorless crystals separated
  2. customwere removed by filtration
  3. washthe filtrate was washed with 50 ml of 1N aqueous citric acid, 50 ml of saturated sodium bicarbonate solution and 80 ml of saturated sodium chloride solution in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe dried filtrate was concentrated in vacuo
  6. customthe yellow, viscous residue (6.8 g) was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-da0aa882333f40deb85f391431eb1a3b
출처 데이터셋
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04888332

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