HCID 131713109, compound → HCID 131713107, compound

HRID 647116Notes

Reaction equation

HRID 647116 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][CH2:3][CH2:2]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][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 131713109HCID 131713109, compound

Product 1

HCID 131713107HCID 131713107, 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 -20° to -12° C. for 45 minutes and at ambient temperature for additional 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-cyclopentyloxyimino-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" (Trade mark, manufactured by Mitsubishi Chemical Industries) (100 ml). After the column was washed with water, elution was carried out with 7.5% 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 pale-yellow powder of 7-[2-cyclopentyloxyimino-2-(4-aminopyrimidin-2-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.67 g), mp 165°-180° 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. waitby standing at 5° C. for 15 hours
  6. washAfter the column was washed with water, elution
  7. additionThe eluates containing a desired compound
  8. customwere collected
  9. customevaporated
  10. customto remove isopropyl alcohol under reduced pressure

Sources & evidence

ORD record
ord-902bbee122134a2bb06d38675a31c2f2
Source dataset
uspto-grants-1983_10
Patent number
US04407798

Reaction notes

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