Hydrochloric Acid → HCID 131716062, compound

HRID 1723594Notes

Reaction equation

HRID 1723594 reaction equation
[CH:1]1([O:4][N:5]=[C:6]([C:27]2[N:28]=[C:29]([NH:32]C=O)[S:30][CH:31]=2)[C:7]([NH:9][C@@H:10]2[C:25](=[O:26])[N:12]3[C:13]([C:22]([OH:24])=[O:23])=[C:14]([CH2:17][O:18][C:19](=[O:21])[NH2:20])[CH2:15][S:16][C@H:11]23)=[O:8])[CH2:3][CH2:2]1.Cl.C(=O)(O)[O-].[Na+]>CO.O1CCCC1>[NH2:32][C:29]1[S:30][CH:31]=[C:27]([C:6](=[N:5][O:4][CH:1]2[CH2:2][CH2:3]2)[C:7]([NH:9][C@@H:10]2[C:25](=[O:26])[N:12]3[C:13]([C:22]([OH:24])=[O:23])=[C:14]([CH2:17][O:18][C:19](=[O:21])[NH2:20])[CH2:15][S:16][C@H:11]23)=[O:8])[N:28]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131716061HCID 131716061, compound

Product 1

HCID 131716062HCID 131716062, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer) (2.0 g) and concentrated hydrochloric acid (1.2 ml) in a mixture of methanol (15 ml) and tetrahydrofuran (15 ml) was warmed at 33° to 35° C. for 1.5 hours. The mixture was poured into ice-water, adjusted to pH 7.5 with saturated aqueous solution of sodium bicarbonate and washed with ethyl acetate. The aqueous solution was adjusted to pH 2 with 1N hydrochloric acid and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with ethyl acetate to give 7β-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer) (0.86 g).

Workup

  1. temperaturewas warmed at 33° to 35° C. for 1.5 hours
  2. washwashed with ethyl acetate
  3. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  4. washThe extract was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-f00b1844e3f1493f89352ec0f6e75c8d
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

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