HCID 131712246, compound → HCID 131712245, compound

HRID 1381365Notes

Reaction equation

HRID 1381365 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:37]1[N:41]=[C:40]([NH2:42])[S:39][N:38]=1)[C:5]([NH:7][CH:8]1[C:35](=[O:36])[N:10]2[C:11]([C:32]([OH:34])=[O:33])=[C:12]([CH2:15][S:16][C:17]3[N:21]([CH2:22][CH2:23][NH:24]C(OC(C)(C)C)=O)[N:20]=[N:19][N:18]=3)[CH2:13][S:14][C@H:9]12)=[O:6]>C(O)=O>[CH3:1][O:2][N:3]=[C:4]([C:37]1[N:41]=[C:40]([NH2:42])[S:39][N:38]=1)[C:5]([NH:7][CH:8]1[C:35](=[O:36])[N:10]2[C:11]([C:32]([OH:34])=[O:33])=[C:12]([CH2:15][S:16][C:17]3[N:21]([CH2:22][CH2:23][NH2:24])[N:20]=[N:19][N:18]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

3

Reactant 1

HCID 131712246HCID 131712246, compound

Product 1

HCID 131712245HCID 131712245, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 7-[2-methoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-[1-{2-(N-t-butoxycarbonylamino)ethyl}-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.0 g) in 99% formic acid (20 ml) was stirred for 2.5 hours at ambient temperatures. The mixture was evaporated to dryness and the residue was dissolved in an aqueous solution of sodium bicarbonate and adjusted to pH 3 with 10% hydrochloric acid. A resulting precipitate was filtered off and the filtrate was subjected to column chromatography on non ion adsorption resin (Dianion HP 20) (Trademark: prepared by Mitsubishi Chemical Industries). The column was washed with water and eluted wth 50% aqueous methanol. The eluate was evaporated to remove methanol and then lyophilized to give 7-[2-methoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-[1-(2-aminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (250 mg). mp 200° to 205° C. (dec.)

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in an aqueous solution of sodium bicarbonate
  3. filtrationA resulting precipitate was filtered off
  4. customthe filtrate was subjected to column chromatography on non ion adsorption resin (Dianion HP 20) (Trademark: prepared by Mitsubishi Chemical Industries)
  5. washThe column was washed with water
  6. washeluted wth 50% aqueous methanol
  7. customThe eluate was evaporated
  8. customto remove methanol

Sources & evidence

ORD record
ord-b2a19660c9c0433297f5b56fdaace670
Source dataset
uspto-grants-1986_04
Patent number
US04585872

Reaction notes

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