Hydrochloric Acid → HCID 131714849, compound

HRID 64755Notes

Reaction equation

HRID 64755 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:37]1[N:38]=[C:39]([NH:42]C=O)[S:40][CH:41]=1)[C:5]([NH:7][CH:8]1[C:35](=[O:36])[N:10]2[C:11]([C:19]([O:21]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:20])=[C:12]([CH:15]=[C:16]([Br:18])[Br:17])[CH2:13][S:14][C@H:9]12)=[O:6].Cl.C(=O)(O)[O-].[Na+]>CO>[CH3:1][O:2][N:3]=[C:4]([C:37]1[N:38]=[C:39]([NH2:42])[S:40][CH:41]=1)[C:5]([NH:7][CH:8]1[C:35](=[O:36])[N:10]2[C:11]([C:19]([OH:21])=[O:20])=[C:12]([CH:15]=[C:16]([Br:17])[Br:18])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131714850HCID 131714850, compound

Product 1

HCID 131714849HCID 131714849, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(2,2-dibromovinyl)-3-cephem-4-carboxylate (syn isomer) (1 g) in methanol (5 ml) was added conc. hydrochloric acid (0.5 ml) and the resulting mixture was stirred at ambient temperature for 2 hours. Then, the reaction mixture was poured into ice-water and adJusted to pH 3.5 with a saturated aqueous solution of sodium bicarbonate. The precipitate was collected by filtration, dried and dissolved in a mixture of trifluoroacetic acid (5 ml) and anisole (0.5 ml) at ambient temperature. After trifluoroacetic acid was evaporated in vacuo, the residue was added to a mixture of ethyl acetate and water and adJusted to pH 3.0 with a saturated aqueous solution of sodium bicarbonate. The separated organic layer was evaporated to give 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(2,2-dibromovinyl)-3-cephem-4-carboxylic acid (syn isomer) (0.35 g).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried
  3. dissolutiondissolved in a mixture of trifluoroacetic acid (5 ml) and anisole (0.5 ml) at ambient temperature
  4. customAfter trifluoroacetic acid was evaporated in vacuo
  5. additionthe residue was added to a mixture of ethyl acetate and water
  6. customThe separated organic layer was evaporated

Sources & evidence

ORD record
ord-0fc0894f9d9d4f4db9f6e705a6b5646b
Source dataset
uspto-grants-1986_09
Patent number
US04609730

Reaction notes

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