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Ethyl Acetate → 1-(Cyclohexyloxycarbonyloxy)Ethyl 7beta-[2-(2-Aminothiazol-4-Yl)Acetamido]-3-Acetoacetoxymethylceph-3-Em-4-Carboxylate

HRID 892924
Notes
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Reaction equation

HRID 892924 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([O-:28])=[O:27])=[C:15]([CH2:18][O:19][C:20](=[O:25])[CH2:21][C:22]([CH3:24])=[O:23])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:32](=[O:44])([O:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[O:33][CH:34](I)[CH3:35].C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([O:28][CH:34]([O:33][C:32]([O:37][CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)=[O:44])[CH3:35])=[O:27])=[C:15]([CH2:18][O:19][C:20](=[O:25])[CH2:21][C:22]([CH3:24])=[O:23])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 111092781-Iodoethyl cyclohexyl carbonateHCID 131715451Sodium 7beta-[2-(2-aminothiazol-4-yl)acetamido]-3-acetoacetoxymethyl-ceph-3-em-4-carboxylate

Product 1

HCID 1317174261-(Cyclohexyloxycarbonyloxy)Ethyl 7beta-[2-(2-Aminothiazol-4-Yl)Acetamido]-3-Acetoacetoxymethylceph-3-Em-4-CarboxylateYield 52.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-5 °C

Procedure

In 30 ml of N,N-dimethylformamide is dissolved 4.76 g of sodium 7β-[2-(2-aminothiazol-4-yl]acetamido]-3-acetoacetoxymethylceph-3-em-4-carboxylate and the solution is cooled to -5° C. With stirring, to the solution is added dropwise 5.0 g of 1-iodoethyl cyclohexyl carbonate, followed by stirring for further 5 minutes. The reaction mixture is poured into a mixture of 300 ml of ethyl acetate and 200 ml of ice water and the organic layer is separated. The aqueous layer is extracted with 200 ml of ethyl acetate. The organic layers are combined and washed with 150 ml each portion of ice water (three times) and saturated aqueous sodium chloride (three times) and then dried over anhydrous magnesium sulfate. The solution is then distilled off under reduced pressure and isopropyl ether is added to the residue. The resultant white powder is collected by filtration, washed with isopropyl ether and dried to obtain 3.3 g of the title compound.

Workup

  1. stirringby stirring for further 5 minutes
  2. customthe organic layer is separated
  3. extractionThe aqueous layer is extracted with 200 ml of ethyl acetate
  4. washwashed with 150 ml each portion of ice water (three times) and saturated aqueous sodium chloride (three times)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solution is then distilled off under reduced pressure and isopropyl ether
  7. additionis added to the residue
  8. filtrationThe resultant white powder is collected by filtration
  9. washwashed with isopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-5ca26217271f40bab34e5766ff77128d
Source dataset
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05120841

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes