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Sodium Bicarbonate → HCID 178508511, compound

HRID 1707481
Notes
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Reaction equation

HRID 1707481 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:73])[C@@H:24]([NH:25][C:26](=[O:72])/[C:27](/[C:47]4[N:48]=[C:49]([NH:52]C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[S:50][CH:51]=4)=[N:28]\[O:29][CH2:30][C:31]([O:33]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:32])[C@H:21]3[S:20][CH2:19][C:18]=2[S:74][CH:75](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:76][C:77]2[N:78]=[N:79][NH:80][CH:81]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].C(=O)([O-])O.[Na+:109]>C(O)=O.O.C1(OC)C=CC=CC=1.Cl>[Na+:109].[NH2:52][C:49]1[S:50][CH:51]=[C:47](/[C:27](=[N:28]/[O:29][CH2:30][C:31]([O:33][Na:109])=[O:32])/[C:26]([NH:25][C@@H:24]2[C:23](=[O:73])[N:22]3[C:17]([C:15]([O-:14])=[O:16])=[C:18]([S:74][CH2:75][S:76][C:77]4[N:78]=[N:79][NH:80][CH:81]=4)[CH2:19][S:20][C@H:21]23)=[O:72])[N:48]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 88301232benzhydryl (6R,7R)-7-[[(2Z)-2-(2-benzhydryloxy-2-oxoethoxy)imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-3-[2,2,2-triphenyl-1-(1H-triazol-4-ylsulfanyl)ethyl]sulfanyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 178508511HCID 178508511, compoundYield 26%

Reagents, catalysts & solvents 4

HCID 284Formic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 7519AnisoleSolvent

Procedure

A solution of 7β-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-(diphenylmethoxycarbonylmethoxyimino)acetamido]-3-(trityl-1,2,3-triazol-4-ylthio-methylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (1.04 g: 0.749 mMol.) in a mixture of 98% formic acid (16 ml) and water (0.8 ml) is stirred at room temperature for 3 hours. The reaction mixture is concentrated. The residue is washed with ether, filtered, end dried. To a solution of this residue in a mixture of anisole (2 ml) and nitro- methane (8 ml) at -40° C. is added a solution of aluminum chloride (0.50 g: 3.76 mMol.) in anisole (2 ml), and the mixture is stirred at -30° to -40° C. for 1 hour. The reaction mixture is diluted with 1N-hydrochloric acid (3.8 ml) and water, washed with ethyl acetate, and concentrated under reduced pressure to remove organic solvents. The remaining aqueous solution is subjected to chromatography over styrene-divinyl-benzene copolymer (methanol: water=4:1). The residue is washed with ethyl acetate and resulting powder is dissolved in dilute aqueous sodium hydrogen carbonate, and purified by chromatography over analytical styrene-divinylbenzene (water). The eluate is lyophilized and pulverized with ethyl acetate to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-(sodiooxycarbonylmethoxyimino)acetamido]-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid sodium salt (121 mg) as pale yellow white powder. Yield: 26%.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. washThe residue is washed with ether
  3. filtrationfiltered
  4. customend dried
  5. additionTo a solution of this residue in a mixture of anisole (2 ml) and nitro- methane (8 ml) at -40° C.
  6. stirringthe mixture is stirred at -30° to -40° C. for 1 hour
  7. washwashed with ethyl acetate
  8. concentrationconcentrated under reduced pressure
  9. customto remove organic solvents
  10. washThe residue is washed with ethyl acetate
  11. customresulting powder
  12. custompurified by chromatography over analytical styrene-divinylbenzene (water)

Sources & evidence

ORD record
ord-93d1996081b74d3283a160aa9eda0f0d
Source dataset
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05352792

Reaction notes

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