Hydrochloric Acid → HCID 141604755, compound

HRID 1247840Notes

Reaction equation

HRID 1247840 reaction equation
[NH2:1][C:2]1[N:3]([CH2:45][CH2:46][OH:47])[N+:4]([CH2:14][C:15]2[CH2:16][S:17][C@@H:18]3[C@H:25]([NH:26][C:27](=[O:43])/[C:28](/[C:37]4[N:41]=[C:40]([NH2:42])[S:39][N:38]=4)=[N:29]\[O:30][C:31]([C:34]([OH:36])=[O:35])([CH3:33])[CH3:32])[C:24](=[O:44])[N:19]3[C:20]=2[C:21]([O-:23])=[O:22])=[CH:5][C:6]=1[N:7]([CH2:10][CH2:11][CH2:12][NH2:13])C=O.Cl.C(=O)([O-])O.[Na+]>CO>[NH2:1][C:2]1[N:3]([CH2:45][CH2:46][OH:47])[N+:4]([CH2:14][C:15]2[CH2:16][S:17][C@@H:18]3[C@H:25]([NH:26][C:27](=[O:43])/[C:28](/[C:37]4[N:41]=[C:40]([NH2:42])[S:39][N:38]=4)=[N:29]\[O:30][C:31]([C:34]([OH:36])=[O:35])([CH3:33])[CH3:32])[C:24](=[O:44])[N:19]3[C:20]=2[C:21]([O-:23])=[O:22])=[CH:5][C:6]=1[NH:7][CH2:10][CH2:11][CH2:12][NH2:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 141604745HCID 141604745, compound

Product 1

HCID 141604755HCID 141604755, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 3-({3-amino-4-[N-(3-aminopropyl)-N-formylamino]-2-(2-hydroxyethyl)-1-pyrazolio}methyl)-7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-cephem-4-carboxylate (100 mg) in methanol (1.4 ml) was added concentrated hydrochloric acid (0.125 ml) at room temperature, and the mixture was stirred for 6.5 hours. To the above solution was added sodium hydrogen carbonate (109 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, made acidic with diluted hydrochloric acid and chromatographed on Diaion® HP20 (Mitsubishi Chemical Corporation) eluting with 20% aqueous 2-propanol. The eluate was concentrated under reduced pressure and lyophilized to give 3-({3-amino-4-[(3-aminopropyl)amino]-2-(2-hydroxyethyl)-1-pyrazolio}methyl)-7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-cephem-4-carboxylate (18 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® HP20 (Mitsubishi Chemical Corporation)
  6. washeluting with 20% aqueous 2-propanol
  7. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c9344db15b5e400886c518d4c90d5091
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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