Hydrochloric Acid → 3-(1-methyl-1H-tetrazol-5-yl) thiomethyl-3-cephem-4-carboxylic acid

HRID 1111437

반응식

HRID 1111437 반응식
[S:1]1[C@@H:6]2[CH2:7][C:8](=[O:9])[N:5]2[C:4]([C:10]([OH:12])=[O:11])=[CH:3][CH2:2]1.[SH:13][C:14]1[N:18]([CH3:19])[N:17]=[N:16][N:15]=1.P(OC)(OC)O[CH3:22].Cl>O1CCCC1.C(Cl)Cl>[CH3:19][N:18]1[C:14]([S:13][CH2:22][C:3]2[CH2:2][S:1][C@@H:6]3[CH2:7][C:8](=[O:9])[N:5]3[C:4]=2[C:10]([OH:12])=[O:11])=[N:15][N:16]=[N:17]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8472Trimethyl phosphiteHCID 52921562(6R)-8-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 178482017HCID 178482017, 화합물

생성물 1

HCID 1186430063-(1-methyl-1H-tetrazol-5-yl) thiomethyl-3-cephem-4-carboxylic acid

시약·촉매·용매 1

HCID 21919333Tetrahydrofurane dichloromethane용매

실험 절차

To 5.03 g of 7β-D-5-carboxy-5-phthalimidovaleramido)-3-cephem-4-carboxylic acid were added 100 ml of tetra-hydrofuran-methylene chloride mixture solution (1:2,v/v), 1.74 g of 5-mercapto-1-methyl-1H-tetrazole and 2.3 ml of trimethyl phosphite in sequence. The reaction was allowed to proceed at 18 to 22° C. for 3.5 hours while stirring. To the reaction solution was added 30 ml of 1N HCl, and the mixture was stirred for 30 minutes, which was concentrated under reduced pressure to about 30 ml. To the concentrate was added 30 ml of methylene chloride, to which was added 1N NaOH to render the pH to 5.6, followed by separating the organic layer from the aqueous layer. To the aqueous layer was added 30 ml of tetrahydrofuran-methylene chloride mixture solution (1:1,v/v), whose pH was changed to 2.0 with 2N HCl, then the organic layer was separated. The aqueous layer was subjected to extraction with 30 ml of the same mixture solution. The organic layers were combined, washed with saturated aqueous saline solution and dried on anhydrous magnesium sulfate, followed by concentration under reduced pressure. The concentrate was poured into 300 ml of ether and the precipitating matter was collected by filtration, washed with ether and dried to obtain 5.86 g (yield:97.4%) of 7β-D-5-carboxy-5-phthalimidovaleramido)-3-(1-methyl-1H-tetrazol-5-yl) thiomethyl-3-cephem-4-carboxylic acid as white powder.

후처리

  1. stirringthe mixture was stirred for 30 minutes
  2. concentrationwhich was concentrated under reduced pressure to about 30 ml
  3. additionTo the concentrate was added 30 ml of methylene chloride
  4. additionto which was added 1N NaOH
  5. customby separating the organic layer from the aqueous layer
  6. additionTo the aqueous layer was added 30 ml of tetrahydrofuran-methylene chloride mixture solution (1:1,v/v), whose pH
  7. customthe organic layer was separated
  8. extractionThe aqueous layer was subjected to extraction with 30 ml of the same mixture solution
  9. washwashed with saturated aqueous saline solution
  10. dry with materialdried on anhydrous magnesium sulfate
  11. concentrationfollowed by concentration under reduced pressure
  12. additionThe concentrate was poured into 300 ml of ether
  13. filtrationthe precipitating matter was collected by filtration
  14. washwashed with ether
  15. customdried

출처 및 근거

ORD 기록
ord-ff526f24317a4725a3d0f92104894f2f
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04980464

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