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Water → 4-Nitrobenzyl 7-(2-phenylacetamido)-3-mesyloxy-3-cephem-4-carboxylate

HRID 434774
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HRID 434774 반응식
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:32](=[O:33])[N:13]3[C:14]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=4)=[O:20])=[C:15]([OH:18])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[S:40](Cl)([CH3:43])(=[O:42])=[O:41].O>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:32](=[O:33])[N:13]3[C:14]([C:19]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=4)=[O:20])=[C:15]([O:18][S:40]([CH3:43])(=[O:42])=[O:41])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 67685788(6S)-4-Nitrobenzyl 3-hydroxy-8-oxo-7-(N-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

생성물 1

HCID 883895734-Nitrobenzyl 7-(2-phenylacetamido)-3-mesyloxy-3-cephem-4-carboxylate수율 70.1%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

4-Nitrobenzyl 7-(2-phenylacetamido)-3-hydroxy-3-cephem-4-carboxylate (100 g.) was dissolved in a mixture of N,N-dimethylformamide (0.4 l.) and tetrahydrofuran (0.4 l.), and thereto was added potassium carbonate (29 g.). To the mixture was added dropwise mesyl chloride (26.3 g.) at 5° C. with stirring, and the stirring was continued at the same temperature for 1.5 hours. After the reaction mixture was poured into a mixture of water (3 l.) and ethyl acetate (3 l.) the organic layer was separated out, washed with water (1 l.) and a saturated aqueous solution of sodium chloride (1 l.×2) and then dried over anhydrous magnesium sulfate, followed by treating with an activated charcoal. The filtrate was concentrated in vacuo, and the precipitated crystals were collected by filtration and washed with diisopropyl ether to give 4-nitrobenzyl 7-(2-phenylacetamido)-3-mesyloxy-3-cephem-4-carboxylate (81.8 g.).

후처리

  1. customwas separated out
  2. washwashed with water (1 l.)
  3. dry with materiala saturated aqueous solution of sodium chloride (1 l.×2) and then dried over anhydrous magnesium sulfate
  4. additionby treating with an activated charcoal
  5. concentrationThe filtrate was concentrated in vacuo
  6. filtrationthe precipitated crystals were collected by filtration
  7. washwashed with diisopropyl ether

출처 및 근거

ORD 기록
ord-670df45099c94397bbc68c5243b174c8
출처 데이터셋
uspto-grants-1983_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04399277

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