Hydrochloric Acid → HCID 44451370, compound

HRID 349540Notes

Reaction equation

HRID 349540 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:37]/[O:38][C:39]([C:42]([OH:44])=[O:43])([CH3:41])[CH3:40])/[C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:32]([O-:34])=[O:33])=[C:15]([CH2:18][N+:19]4[N:20]([CH3:31])[C:21]([NH:28]C=O)=[C:22]([CH2:24][NH:25]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:37]/[O:38][C:39]([C:42]([OH:44])=[O:43])([CH3:41])[CH3:40])/[C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:32]([O-:34])=[O:33])=[C:15]([CH2:18][N+:19]4[N:20]([CH3:31])[C:21]([NH2:28])=[C:22]([CH2:24][NH2:25])[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 141601001HCID 141601001, compound

Product 1

HCID 44451370HCID 44451370, compoundYield 2.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-(3-formamido-4-formamidomethyl-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (2.5 g) in methanol (25 ml) was added concentrated hydrochloric acid (2.5 ml) at room temperature. The mixture was stirred at room temperature for 17 hours. The reaction mixture was adjusted to about pH 7 with saturated aqueous sodium hydrogencarbonate solution and concentrated in vacuo to remove methanol. The resulting residue was purified by preparative HPLC utilizing ODS column. The eluate containing a desired product was concentrated to about 30 ml in vacuo. The concentrate was adjusted to about pH 1 with concentrated hydrochloric acid and chromatographed on Diaion® HP-20 (Mitsubishi Chemical Corporation) eluting with 20% aqueous 2-propanol. The eluate was concentrated in vacuo 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-aminomethyl-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (50 mg) as an amorphous solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove methanol
  3. customThe resulting residue was purified by preparative HPLC utilizing ODS column
  4. additionThe eluate containing a desired product
  5. concentrationwas concentrated to about 30 ml in vacuo
  6. customchromatographed on Diaion®
  7. wash(Mitsubishi Chemical Corporation) eluting with 20% aqueous 2-propanol
  8. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-ffd41ff9d21046d38abcf304f5ca0aa8
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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