Hydrochloric Acid → HCID 131716057, compound

HRID 1074354Notes

Reaction equation

HRID 1074354 reaction equation
[CH:1]1([O:4][N:5]=[C:6]([C:29]2[N:33]=[C:32]([NH:34]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:31][N:30]=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>[NH2:34][C:32]1[S:31][N:30]=[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:33]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131716058HCID 131716058, compound

Product 1

HCID 131716057HCID 131716057, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of 7β-[2-(cyclopropyloxyimino)-2-(5-tritylamino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.1 g) in formic acid (11 ml) was added concentrated hydrochloric acid (0.29 ml) under ice-cooling. The mixture was stirred for 3.5 hours at the same temperature. The mixture was concentrated in vacuo and poured into a mixture of ethyl acetate and water. After the mixture was adjusted to pH 7.2 with saturated aqueous solution of sodium bicarbonate, the aqueous layer was separated, adjusted to pH 3 with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate, concentrated in vacuo, and triturated with diethyl ether to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(cyclopropyloxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (459 mg) as a solid.

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated in vacuo
  3. additionpoured into a mixture of ethyl acetate and water
  4. customthe aqueous layer was separated
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-b26f912246374ef49678d9f51b37c8af
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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