Hydrochloric Acid → HCID 88649771, compound

HRID 569137Notes

Reaction equation

HRID 569137 reaction equation
Cl.[C:2]([O:8][CH2:9][O:10][C:11]([C:13]1[N:18]2[C:19](=[O:41])[C@@H:20]([NH:21][C:22](=[O:40])/[C:23](/[C:27]3[N:28]=[C:29]([NH:32]C(OC(C)(C)C)=O)[S:30][CH:31]=3)=[CH:24]\[CH2:25][CH3:26])[C@H:17]2[S:16][CH2:15][CH:14]=1)=[O:12])(=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4]>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[C:2]([O:8][CH2:9][O:10][C:11]([C:13]1[N:18]2[C:19](=[O:41])[C@@H:20]([NH:21][C:22](=[O:40])/[C:23](/[C:27]3[N:28]=[C:29]([NH2:32])[S:30][CH:31]=3)=[CH:24]\[CH2:25][CH3:26])[C@H:17]2[S:16][CH2:15][CH:14]=1)=[O:12])(=[O:7])[C:3]([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 88650330HCID 88650330, compound

Product 1

HCID 88649771HCID 88649771, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

[Hydrochloride] A solution of 7beta-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl]amino-3-cephem-4-carboxylic acid pivaloyloxymethyl ester (360 mg) in a mixture of anisole (2 ml) and trifluoroacetic acid (2 ml) is stirred at room temperature for 150 minutes and concentrated. The residue is dissolved in aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The extract is purified by silica gel column chromatography to give 7beta-[(Z)-2-(2-aminothiazol-4-yl)-2-pentenoyl]amino-3-cephem-4-carboxylic acid pivaloyloxymethyl ester (250 mg). This is dissolved in dichloromethane, mixed with a solution of hydrochloric acid in ethyl acetate, and concentrated. The crystalline residue is washed with ether to give the hydrochloride of above ester.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in aqueous sodium hydrogen carbonate
  3. extractionextracted with ethyl acetate
  4. customThe extract is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a8723316ef8548e6a22eb2e2a6859ebd
Source dataset
uspto-grants-1988_03
Patent number
US04731361

Reaction notes

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