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Sodium Bicarbonate → Cefamandole Sodium

HRID 2285638
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HRID 2285638 반응식
[C:1]([NH:11][C@@H:12]1[C:34](=[O:35])[N:14]2[C:15]([C:31]([OH:33])=[O:32])=[C:16]([CH2:19]OC(=O)C(C3C=CC=CC=3)O)[CH2:17][S:18][C@H:13]12)(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[SH:36][C:37]1[N:41]([CH3:42])[N:40]=[N:39][N:38]=1.C(=O)([O-])O.[Na+:47]>O>[Na+:47].[C:1]([NH:11][C@@H:12]1[C:34](=[O:35])[N:14]2[C:15]([C:31]([O-:33])=[O:32])=[C:16]([CH2:19][S:36][C:37]3[N:41]([CH3:42])[N:40]=[N:39][N:38]=3)[CH2:17][S:18][C@H:13]12)(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]
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참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 131712065HCID 131712065, 화합물HCID 178482017HCID 178482017, 화합물

생성물 1

HCID 23672568Cefamandole Sodium수율 70%

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

In water (5 ml) was dissolved 7β-(D-mandelamido)-3-mandelyloxymethyl-3-cephem-4-carboxylic acid (0.50 g) together with 5-mercapto-1-methyl-1H-tetrazole (0.12 g) and sodium hydrogen carbonate (0.17 g). The solution was stirred at 60° C. for 30 minutes. After cooling in the air, the reaction mixture was subjected to column chromatography on Amberlite XAD-2, elution being carried out with water and a solvent mixture of water and methanol. The fractions containing the desired product were pooled, concentrated and lyophilized. The procedure provided 7β-(D-mandelamido)-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid sodium salt (0.34 g).

후처리

  1. temperatureAfter cooling in the air
  2. washthe reaction mixture was subjected to column chromatography on Amberlite XAD-2, elution
  3. additiona solvent mixture of water and methanol
  4. additionThe fractions containing the desired product
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f287a355636146f9937d003caf0a8029
출처 데이터셋
uspto-grants-1982_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04323676

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