Chlorotrimethylsilane → 7-(Di-2-thienylacetyl)amino-3-acetoxymethyl-3-cephem-4-carboxylic acid

HRID 66695

반응식

HRID 66695 반응식
[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:23][S:22][C@@H:9]2[C@H:10]([NH:13][C:14]([CH2:16][C:17]3[S:21][CH:20]=[CH:19][CH:18]=3)=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:24]([O-:26])=[O:25])=[O:3].[Na+].C[Si](C)(C)Cl.[SiH3]NC(=O)C(F)(F)F.[S:41]1[CH:45]=[CH:44][CH:43]=[C:42]1CC(Cl)=O>C(Cl)(Cl)Cl>[S:21]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:16]([C:42]1[S:41][CH:45]=[CH:44][CH:43]=1)[C:14]([NH:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:24]([OH:26])=[O:25])=[C:6]([CH2:5][O:4][C:2](=[O:3])[CH3:1])[CH2:23][S:22][C@H:9]12)=[O:15]

참가 물질

6

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 1623622-Thiopheneacetyl chlorideHCID 23675321Cephalothin SodiumHCID 123231972Monosilyltrifluoroacetamide

생성물 1

HCID 705412177-(Di-2-thienylacetyl)amino-3-acetoxymethyl-3-cephem-4-carboxylic acid

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
45 °C

실험 절차

A suspension of sodium cephalothin (1.18 g.) in anhydrous alcohol-free chloroform (10 ml.) is silylated by the addition of trimethylchlorosilane (1.1 ml.). After stirring for 30 minutes, monosilyltrifluoroacetamide (2.5 ml.) and 2-thienylacetyl chloride (2.0 ml.) are added to the suspension which is then heated to 45° C. The mixture is allowed to remain at this temperature for two days and then evaporated in vacuo to a residue which is dissolved in ethyl acetate (50 ml.) and washed three times with water. The ethyl acetate layer is dried over magnesium sulfate, filtered and the filtrate evaporated in vacuo to obtain a residue. The residue is dissolved in chloroform and precipitated with hexane three times, each time discarding the supernatent liquid. The 7-(di-2-thienylacetyl)amino-3-acetoxymethyl-3-cephem-4-carboxylic acid is obtained in a solvent-free form by freeze-drying from a solution in benzene.

후처리

  1. waitto remain at this temperature for two days
  2. customevaporated in vacuo to a residue which
  3. dissolutionis dissolved in ethyl acetate (50 ml.)
  4. washwashed three times with water
  5. dry with materialThe ethyl acetate layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customto obtain a residue
  9. customprecipitated with hexane three times

출처 및 근거

ORD 기록
ord-5ff319df6c5b47bba3a595b68dcf6c08
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04342869

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