Ethyl Acetate → HCID 131714952, compound

HRID 1731690Notes

Reaction equation

HRID 1731690 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH3:15])[C:10]([OH:12])=O)[N:8]=1)=[O:2].[NH2:16][CH:17]1[C:50](=[O:51])[N:19]2[C:20]([C:34]([O:36][CH:37]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])=[C:21]([CH2:24][S:25]/[CH:26]=[CH:27]\[C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[CH2:22][S:23][C@H:18]12.C[Si](NC(=O)N[Si](C)(C)C)(C)C.C(OCC)(=O)C>O1CCCC1.O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH3:15])[C:10]([NH:16][CH:17]2[C:50](=[O:51])[N:19]3[C:20]([C:34]([O:36][CH:37]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)=[O:35])=[C:21]([CH2:24][S:25]/[CH:26]=[CH:27]\[C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)[CH2:22][S:23][C@H:18]23)=[O:12])[N:8]=1)=[O:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 875621,3-Bis(trimethylsilyl)ureaHCID 27245112-(2-Formylamino-1,3-Thiazol-4-Yl)-2-(Methoxyimino)Acetic AcidHCID 13456894HCID 13456894, compound

Product 1

HCID 131714952HCID 131714952, compoundYield 37.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer) (1.06 g) was added to the mixture at 0° C. The mixture was stirred for 30 minutes at the same temperature to give an activated acid solution. On the other hand, to the suspension of benzhydryl 7-amino-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate (2.38 g) in tetrahydrofuran (30 ml) was added bis(trimethylsilyl)urea (2.8 g) at ambient temperature. The mixture was stirred at 48° C. for 30 minutes to give a clear solution. The solution was cooled to -20° C. To this solution was added the activated acid solution obtained above at once at -20° C. The mixture was stirred at -20°~-12° C. for 40 minutes. To this mixture was added a mixture of ethyl acetate (150 ml) and water. The separated organic layer was washed with an aqueous solution of sodium bicarbonate, dried over magnesium sulfate and concentrated in vacuo to give a solid. The solid was recrystallized from ethyl acetate to give benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate (syn isomer) (1.26 g).

Workup

  1. customto give an activated acid solution
  2. stirringThe mixture was stirred at 48° C. for 30 minutes
  3. customto give a clear solution
  4. additionTo this solution was added the activated acid solution
  5. customobtained above at once at -20° C
  6. stirringThe mixture was stirred at -20°~-12° C. for 40 minutes
  7. additionTo this mixture was added
  8. washThe separated organic layer was washed with an aqueous solution of sodium bicarbonate
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customto give a solid
  12. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d386ada04d4949779b7c2ec8f05c9781
Source dataset
uspto-grants-1986_11
Patent number
US04622318

Reaction notes

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