Hydrochloric Acid → HCID 131716049, compound

HRID 1074351Notes

Reaction equation

HRID 1074351 reaction equation
[CH:1]1([O:4][N:5]=[C:6]([C:29]2[N:30]=[C:31]([NH:34]C=O)[S:32][CH:33]=2)[C:7]([NH:9][C@@H:10]2[C:27](=[O:28])[N:12]3[C:13]([C:24]([OH:26])=[O:25])=[C:14]([CH2:17][S:18][C:19]4[S:20][CH:21]=[N:22][N:23]=4)[CH2:15][S:16][C@H:11]23)=[O:8])[CH2:3][CH2:2]1.Cl.C(=O)(O)[O-].[Na+]>CO>[NH2:34][C:31]1[S:32][CH:33]=[C:29]([C:6](=[N:5][O:4][CH:1]2[CH2:3][CH2:2]2)[C:7]([NH:9][C@@H:10]2[C:27](=[O:28])[N:12]3[C:13]([C:24]([OH:26])=[O:25])=[C:14]([CH2:17][S:18][C:19]4[S:20][CH:21]=[N:22][N:23]=4)[CH2:15][S:16][C@H:11]23)=[O:8])[N:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131716722HCID 131716722, compound

Product 1

HCID 131716049HCID 131716049, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.1 g) and concentrated hydrochloric acid (0.404 ml) in methanol (10.5 ml) was warmed at 33°-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-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (786 mg).

Workup

  1. temperaturewas warmed at 33°-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-115387b8194d48df86775887bbc063a7
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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