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Potassium Phosphate, Dibasic → 3-Acetoxymethyl-7beta-[2-(5-tert.-butoxycarbonylaminomethyl-2-thienyl)-acetylamino]-3-cephem-4-carboxylic acid tert.-butyl ester

HRID 224905
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HRID 224905 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:14][C:13]([CH2:15][C:16]([OH:18])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(Cl)=O)C(C)C.[C:27]([O:31][C:32]([C:34]1[N:39]2[C:40](=[O:43])[C@@H:41]([NH2:42])[C@H:38]2[S:37][CH2:36][C:35]=1[CH2:44][O:45][C:46](=[O:48])[CH3:47])=[O:33])([CH3:30])([CH3:29])[CH3:28].P([O-])([O-])(O)=O.[K+].[K+]>C(Cl)Cl.CN1CCOCC1>[C:27]([O:31][C:32]([C:34]1[N:39]2[C:40](=[O:43])[C@@H:41]([NH:42][C:16](=[O:18])[CH2:15][C:13]3[S:14][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:11][CH:12]=3)[C@H:38]2[S:37][CH2:36][C:35]=1[CH2:44][O:45][C:46](=[O:48])[CH3:47])=[O:33])([CH3:30])([CH3:28])[CH3:29]
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7

반응물 4

HCID 24450Potassium Phosphate, DibasicHCID 62365Isobutyl chloroformateHCID 15573427tert-butyl (6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 202932812-[5-({[(Tert-butoxy)carbonyl]amino}methyl)thiophen-2-yl]aceticacid

생성물 1

HCID 70596567
3-Acetoxymethyl-7beta-[2-(5-tert.-butoxycarbonylaminomethyl-2-thienyl)-acetylamino]-3-cephem-4-carboxylic acid tert.-butyl ester

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 79724-Methylmorpholine용매

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온도
-20 °C

실험 절차

The starting material can be prepared as follows: 8.15 g of 2-(5-tert.-butoxycarbonylaminomethyl-2-thienyl)-acetic acid are dissolved in 500 ml of methylene chloride containing 3.06 ml of N-methylmorpholine, the solution, from which moisture is kept excluded, is cooled to -20° C. and 4.13 ml of chloroformic acid isobutyl ester are added dropwise whilst keeping the temperature at between -15° C. and -20° C. After 30 minutes, a solution of 9.85 g of 3-acetoxymethyl-7β-amino-3-cephem-4-carboxylic acid tert.-butyl ester in 50 ml of methylene chloride is added, after which the solution is stirred for a further 15 hours whilst slowly raising the temperature to 20° C. to 25° C. The mixture is poured out into ice-cold water, neutralised with dipotassium hydrogen phosphate and extracted repeatedly with methylene chloride. The organic extracts are washed with an aqueous saturated sodium chloride solution and dried over magnesium sulphate, after which the solvent is removed under reduced pressure. The residue is recrystallised from diethyl ether and gives 3-acetoxymethyl-7β-[2-(5-tert.-butoxycarbonylaminomethyl-2-thienyl)-acetylamino]-3-cephem-4-carboxylic acid tert.-butyl ester, melting point 76°-78° C., thin layer chromatogram (silica gel): Rf=0.44 (system: chloroform/ethyl acetate/acetic acid, 80:19:1).

후처리

  1. customThe starting material can be prepared
  2. customat between -15° C. and -20° C
  3. temperatureslowly raising the temperature to 20° C. to 25° C
  4. additionThe mixture is poured out into ice-cold water
  5. extractionextracted repeatedly with methylene chloride
  6. washThe organic extracts are washed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. customafter which the solvent is removed under reduced pressure
  9. customThe residue is recrystallised from diethyl ether

출처 및 근거

ORD 기록
ord-7791b97ce8bc41b88ad4ddddf756f336
출처 데이터셋
uspto-grants-1980_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04234578

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