5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[2-[2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-thiazolyl]-1-oxo-2-butenyl]amino]-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, [6R-[6α,7β(Z)]]- → HCID 10099150, compound

HRID 569135Notes

Reaction equation

HRID 569135 reaction equation
[C:1]([O:7][CH2:8][O:9][C:10]([C:12]1[N:17]2[C:18](=[O:39])[C@@H:19]([NH:20][C:21](=[O:38])/[C:22](/[C:25]3[N:26]=[C:27]([NH:30]C(OC(C)(C)C)=O)[S:28][CH:29]=3)=[CH:23]\[CH3:24])[C@H:16]2[S:15][CH2:14][C:13]=1[CH2:40][O:41][C:42](=[O:44])[NH2:43])=[O:11])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>FC(F)(F)C(O)=O>[C:1]([O:7][CH2:8][O:9][C:10]([C:12]1[N:17]2[C:18](=[O:39])[C@@H:19]([NH:20][C:21](=[O:38])/[C:22](/[C:25]3[N:26]=[C:27]([NH2:30])[S:28][CH:29]=3)=[CH:23]\[CH3:24])[C@H:16]2[S:15][CH2:14][C:13]=1[CH2:40][O:41][C:42](=[O:44])[NH2:43])=[O:11])(=[O:6])[C:2]([CH3:5])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 100094965-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[2-[2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-thiazolyl]-1-oxo-2-butenyl]amino]-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, [6R-[6α,7β(Z)]]-

Product 1

HCID 10099150HCID 10099150, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7beta-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-butenoyl]amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid pivaloyloxymethyl ester (160 mg) in trifluoroacetic acid (2 ml) is stirred at room temperature for 120 minutes and concentrated. To the resulting residue is added aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The extract solution is purified by silica gel chromatography to give 7beta-[(Z)-2-(2-aminothiazol-4-yl)-2-butenoyl]amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid pivaloyloxymethyl ester (75 mg).

Workup

  1. concentrationconcentrated
  2. additionTo the resulting residue is added aqueous sodium hydrogen carbonate
  3. extractionextracted with ethyl acetate
  4. customThe extract solution is purified by silica gel chromatography

Sources & evidence

ORD record
ord-71da1dde8bc947b09dfe03f924dc2b01
Source dataset
uspto-grants-1988_03
Patent number
US04731361

Reaction notes

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