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Potassium Carbonate → benzhydryl (6R,7R)-7-[[(2Z)-2-[4,5-bis[(2-chloroacetyl)oxy]-2-methylbenzoyl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[(7-methyl-5-oxo-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1200295
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HRID 1200295 반응식
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:18]3[C@H:21]([S:22][CH2:23][C:24]=2[CH2:25][S:26][C:27]2[S:37][C:30]4=[N:31][C:32]([CH3:36])=[CH:33][C:34](=[O:35])[N:29]4[N:28]=2)[C@H:20]([NH:38][C:39](=[O:68])/[C:40](/[C:43]2[N:44]=[C:45]([NH:48][C:49]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[S:46][CH:47]=2)=[N:41]\[OH:42])[C:19]3=[O:69])=[O:16])[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(=O)([O-])[O-].[K+].[K+].[Cl:76][CH2:77][C:78]([O:80][C:81]1[C:89]([O:90][C:91](=[O:94])[CH2:92][Cl:93])=[CH:88][C:84]([C:85](Cl)=[O:86])=[C:83]([CH3:95])[CH:82]=1)=[O:79]>ClCCl>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:18]3[C@H:21]([S:22][CH2:23][C:24]=2[CH2:25][S:26][C:27]2[S:37][C:30]4=[N:31][C:32]([CH3:36])=[CH:33][C:34](=[O:35])[N:29]4[N:28]=2)[C@H:20]([NH:38][C:39](=[O:68])/[C:40](/[C:43]2[N:44]=[C:45]([NH:48][C:49]([C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=4)([C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=4)[C:62]4[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=4)[S:46][CH:47]=2)=[N:41]\[O:42][C:85](=[O:86])[C:84]2[CH:88]=[C:89]([O:90][C:91](=[O:94])[CH2:92][Cl:93])[C:81]([O:80][C:78](=[O:79])[CH2:77][Cl:76])=[CH:82][C:83]=2[CH3:95])[C:19]3=[O:69])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 141247204,5-Bis(chloroacetoxy)-2-methylbenzoyl chlorideHCID 16166547benzhydryl (6R,7R)-7-[[(2Z)-2-hydroxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[(7-methyl-5-oxo-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

생성물 1

HCID 16166549
benzhydryl (6R,7R)-7-[[(2Z)-2-[4,5-bis[(2-chloroacetyl)oxy]-2-methylbenzoyl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[(7-methyl-5-oxo-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
수율 60%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To an ice-cooled solution of the product obtained in Step 4 (0.6 g) in dry dichloromethane (15 ml) was added potassium carbonate (0.1 g) at once, followed by dropwise addition of a solution of 4,5-bis(chloroacetoxy)-2-methylbenzoyl chloride (0.25 g) in dry dichloromethane (10 ml). The mixture was stirred under ice cooling for one hour and then at room temperature for an additional two hours. After filtering off the insoluble matters, the filtrate was washed with water and 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 0.47 g of the objective compound.

후처리

  1. waitat room temperature for an additional two hours
  2. filtrationAfter filtering off the insoluble matters
  3. washthe filtrate was washed with water and with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe dried solution was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-430db487cd224385bbb55b8342ee086c
출처 데이터셋
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04904791

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