Hydrochloric Acid → HCID 141604773, compound

HRID 1247810Notes

Reaction equation

HRID 1247810 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:38]/[O:39][C:40]([C:43]([OH:45])=[O:44])([CH3:42])[CH3:41])/[C:8]([NH:10][C@@H:11]2[C:36](=[O:37])[N:13]3[C:14]([C:33]([O-:35])=[O:34])=[C:15]([CH2:18][N+:19]4[N:20]([CH3:32])[C:21]([NH2:31])=[C:22]([N:24]([CH2:27][CH2:28][CH2:29][NH2:30])C=O)[CH:23]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.Cl.C(=O)([O-])O.[Na+]>CO>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:38]/[O:39][C:40]([C:43]([OH:45])=[O:44])([CH3:42])[CH3:41])/[C:8]([NH:10][C@@H:11]2[C:36](=[O:37])[N:13]3[C:14]([C:33]([O-:35])=[O:34])=[C:15]([CH2:18][N+:19]4[N:20]([CH3:32])[C:21]([NH2:31])=[C:22]([NH:24][CH2:27][CH2:28][CH2:29][NH2:30])[CH:23]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 141604769HCID 141604769, compound

Product 1

HCID 141604773HCID 141604773, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-{3-amino-4-[N-(3-aminopropyl)-N-formylamino]-2-methyl-1-pyrazolio}methyl-3-cephem-4-carboxylate (140 mg) in methanol (2.6 ml) was added concentrated hydrochloric acid (0.176 ml) at room temperature, and the mixture was stirred for 6.5 hours. To the reaction mixture was added sodium hydrogen carbonate (177 mg), and the mixture was purified by preparative HPLC (ODS column, acetonitrile/phosphate buffer (pH 7)=5:95). The eluate containing a desired product was evaporated to remove acetonitrile, acidified with diluted hydrochloric acid and chromatographed on Diaion® HP-20 eluting with 20% aqueous 2-propanol. The eluate was concentrated under reduced pressure and lyophilized to give 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-{3-amino-4-[(3-aminopropyl)amino]-2-methyl-1-pyrazolio}methyl-3-cephem-4-carboxylate (39 mg).

Workup

  1. customthe mixture was purified by preparative HPLC (ODS column, acetonitrile/phosphate buffer (pH 7)=5:95)
  2. additionThe eluate containing a desired product
  3. customwas evaporated
  4. customto remove acetonitrile
  5. customchromatographed on Diaion® HP-20
  6. washeluting with 20% aqueous 2-propanol
  7. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d0bc296603154ae498b60343e48f1e10
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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