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Dicyclohexylcarbodiimide → HCID 141557382, 화합물

HRID 1032197
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HRID 1032197 반응식
[C:1]1([C:7]([NH:20][C:21]2[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH:32]([C:51]([O:53][CH:54]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[O:52])[C:33]3[CH:38]=[C:37]([O:39][C:40](=[O:42])[CH3:41])[C:36]([O:43][C:44](=[O:46])[CH3:45])=[C:35]([O:47][C:48](=[O:50])[CH3:49])[CH:34]=3)/[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:67]1([CH:73]([O:80][C:81]([C:83]2[N:84]3[C@H:87]([S:88][CH2:89][C:90]=2[CH2:91][S:92][C:93]2[N:98]4[N:99]=[C:100]([C:102]([O:104][CH:105]([C:112]5[CH:117]=[CH:116][CH:115]=[CH:114][CH:113]=5)[C:106]5[CH:111]=[CH:110][CH:109]=[CH:108][CH:107]=5)=[O:103])[N:101]=[C:97]4[N:96]=[C:95]([CH3:118])[CH:94]=2)[C@H:86]([NH2:119])[C:85]3=[O:120])=[O:82])[C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:67]1([CH:73]([O:80][C:81]([C:83]2[N:84]3[C@H:87]([S:88][CH2:89][C:90]=2[CH2:91][S:92][C:93]2[N:98]4[N:99]=[C:100]([C:102]([O:104][CH:105]([C:112]5[CH:113]=[CH:114][CH:115]=[CH:116][CH:117]=5)[C:106]5[CH:107]=[CH:108][CH:109]=[CH:110][CH:111]=5)=[O:103])[N:101]=[C:97]4[N:96]=[C:95]([CH3:118])[CH:94]=2)[C@H:86]([NH:119][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:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[S:22][CH:23]=2)=[N:30]\[O:31][CH:32]([C:51]([O:53][CH:54]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[O:52])[C:33]2[CH:38]=[C:37]([O:39][C:40](=[O:42])[CH3:41])[C:36]([O:43][C:44](=[O:46])[CH3:45])=[C:35]([O:47][C:48](=[O:50])[CH3:49])[CH:34]=2)[C:85]3=[O:120])=[O:82])[C:74]2[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=2)[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 13821813HCID 13821813, 화합물HCID 14479215(2Z)-2-[2-benzhydryloxy-2-oxo-1-(3,4,5-triacetyloxyphenyl)ethoxy]imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid

생성물 1

HCID 141557382HCID 141557382, 화합물

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To an ice-cooled solution containing the product obtained in Step 4 (2.2 g) and (6R,7R)-7-amino-3-[(2-diphenylmethyloxycarbonyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester (1.84 g) in dichloromethane (65 ml) was added dicyclohexylcarbodiimide (0.59 g), and the mixture was stirred overnight at room temperature. The insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the insoluble matters were removed by filtration. The filtrate was washed with brine and dried over anhydrous sodium sulfate. The dried solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, giving 0.86 g (less polar form) and 0.94 g (more polar form) of the objective compound.

후처리

  1. filtrationThe insoluble matters were filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. customthe insoluble matters were removed by filtration
  5. washThe filtrate was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe dried solution was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography
  9. customgiving 0.86 g (less polar form) and 0.94 g (more polar form) of the objective compound

출처 및 근거

ORD 기록
ord-2d5c348578bb4df2b8ad43a2663ca797
출처 데이터셋
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04956474

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