Hydrochloric Acid → Diphenylmethyl 7beta-amino-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylate

HRID 992691Notes

Reaction equation

HRID 992691 reaction equation
C([NH:3][C@@H:4]1[C:33](=[O:34])[N:6]2[C:7]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:8]([S:11][C:12]3[S:16][N:15]=[N:14][CH:13]=3)[CH2:9][S:10][C@H:5]12)=O.Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CO.C1COCC1>[NH2:3][C@@H:4]1[C:33](=[O:34])[N:6]2[C:7]([C:17]([O:19][CH:20]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:8]([S:11][C:12]3[S:16][N:15]=[N:14][CH:13]=3)[CH2:9][S:10][C@H:5]12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 88157740Diphenylmethyl 7beta-formamido-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylate

Product 1

HCID 70122870Diphenylmethyl 7beta-amino-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylateYield 85.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diphenylmethyl 7β-formamido-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylate (3.99 g) in a mixture of methanol (20 ml) and THF (10 ml) was added concentrated hydrochloric acid (2.75 ml) at the room temperature. After stirring at the same temperature for 4 hours, the mixture was poured into a mixture of ice water and ethyl acetate. The mixture was adjusted to pH 4 with aqueous sodium bicarbonate solution. The organic layer was separated washed with water and brine, dried over magnesium sulfate, and evaporated to give diphenylmethyl 7β-amino-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylate (3.24 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-89235951e9af403688379d54fe34d448
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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