Hydrochloric Acid → benzhydryl (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

HRID 1200294노트

반응식

HRID 1200294 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:73])/[C:40](/[C:48]2[N:49]=[C:50]([NH:53][C:54]([C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)([C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)[C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)[S:51][CH:52]=2)=[N:41]\[O:42]C(OC)(C)C)[C:19]3=[O:74])=[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.Cl.C(OCC)(=O)C>CC(C)=O>[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:73])/[C:40](/[C:48]2[N:49]=[C:50]([NH:53][C:54]([C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=4)([C:61]4[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=4)[C:67]4[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=4)[S:51][CH:52]=2)=[N:41]\[OH:42])[C:19]3=[O:74])=[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 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 16166545benzhydryl (6R,7R)-7-[[(2Z)-2-(2-methoxypropan-2-yloxyimino)-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 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-carboxylate수율 75.8%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of the product obtained in Step 3 (1.5 g) in acetone (12 ml) was added 1N hydrochloric acid 2.6 ml), and the resulting solution was stirred at room temperature for 3.5 hours. Ethyl acetate was added to the solution, and the organic layer was washed with water, 5% sodium bicarbonate solution and brine in that order, 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 1.06 g of the objective compound as milky white crystals.

후처리

  1. washthe organic layer was washed with water, 5% sodium bicarbonate solution and brine in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe dried solution was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f240e2472512477cb41ecfdffdc191d2
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04904791

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