HCID 131713113, compound → HCID 131713111, compound

HRID 647117Notes

Reaction equation

HRID 647117 reaction equation
[CH:1]1([O:6][N:7]=[C:8]([C:31]2[N:36]=[C:35]([NH:37]C=O)[CH:34]=[CH:33][N:32]=2)[C:9]([NH:11][CH:12]2[C:29](=[O:30])[N:14]3[C:15]([C:26]([O-:28])=[O:27])=[C:16]([CH2:19][N+:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1>C(=O)(O)[O-].[Na+]>[CH:1]1([O:6][N:7]=[C:8]([C:31]2[N:36]=[C:35]([NH2:37])[CH:34]=[CH:33][N:32]=2)[C:9]([NH:11][CH:12]2[C:29](=[O:30])[N:14]3[C:15]([C:26]([O-:28])=[O:27])=[C:16]([CH2:19][N+:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

3

Reactant 1

HCID 131713113HCID 131713113, compound

Product 1

HCID 131713111HCID 131713111, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

This solution was added to the activated acid solution prepared above, and the mixture was stirred at -19° to -10° C. for half an hour and at ambient temperature for additional half an hour. The reaction mixture was poured into an aqueous solution (100 ml) of sodium bicarbonate (8.47 g). The aqueous layer containing 7-[2-(2-cyclopenten-1-yloxyimino)-2-(4-formamidopyrimidin-2-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) was separated out, adjusted to pH 1 with 6 N hydrochloric acid and washed with ethyl acetate, followed by standing at 5° C. for 15 hours. This aqueous solution was subjected to column chromatography on a non-ionic adsorption resin "Diaion HP-20" (200 ml). After the column was washed with water, elution was carried out with 10% aqueous isopropyl alcohol. The eluates containing a desired compound were collected, evaporated to remove isopropyl alcohol under reduced pressure. The resultant solution was lyophilized to give yellowish white powder of 7-[2-(2-cyclopenten-1-yloxyimino)-2-(4-aminopyrimidin-2-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.97 g), mp 160°-175° C. (dec.).

Workup

  1. additionThis solution was added to the activated acid solution
  2. customprepared above, and the mixture
  3. customwas separated out
  4. washwashed with ethyl acetate
  5. washAfter the column was washed with water, elution
  6. additionThe eluates containing a desired compound
  7. customwere collected
  8. customevaporated
  9. customto remove isopropyl alcohol under reduced pressure

Sources & evidence

ORD record
ord-f16355ed17184438bf096ef3e8139372
Source dataset
uspto-grants-1983_10
Patent number
US04407798

Reaction notes

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