Sodium Iodide →

HRID 2232066Notes

Reaction equation

HRID 2232066 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:28]/[O:29][C@H:30]2[CH2:34][CH2:33][NH:32][C:31]2=[O:35])/[C:8]([NH:10][C@@H:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([OH:25])=[O:24])=[C:15]([CH2:18]OC(=O)C)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[CH3:36][N:37]1[C:42](=[S:43])[CH:41]=[CH:40][CH:39]=[CH:38]1.[I-].[Na+].C(=O)([O-])O.[Na+]>O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:28]/[O:29][C@H:30]2[CH2:34][CH2:33][NH:32][C:31]2=[O:35])/[C:8]([NH:10][C@@H:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([O-:25])=[O:24])=[C:15]([CH2:18][S:43][CH2+:42]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]4[CH3:36])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 162771-Methyl-2(1H)-pyridinethioneHCID 516892Sodium BicarbonateHCID 13556686HCID 13556686, compound

Product 0

No Product data yet.

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To 4.8 ml of water are added 341 mg of 7β{(Z)-2-(2-aminothiazol-4-yl)-2-[((3S)-2-oxopyrrolidin-3-yl)oxyimino]acetamido}-3-acetoxymethyl-3-cephem-4-carboxylic acid, 125 mg of 1-methyl-2-thiopyridone and 900 mg of sodium iodide. The mixture is adjusted to a pH of 6.63 with an aqueous solution of sodium hydrogencarbonate. The mixture is stirred in an argon atmosphere at 65° C. for 3.5 hours. The reaction mixture is concentrated under reduced pressure. The concentrate is introduced into a column packed with HP-20 and is eluted with 20% and 25% methanol solutions. The fractions containing the contemplated compound are collected and concentrated. The residue is lyophilized, giving 128 mg of 7β-{(Z)-2-(2-aminothiazol-4-yl)-2-[((3S)-2-oxopyrrolidin-3-yl)oxyimino]acetamido}-3-(1-methyl-2-pyridinio)thiomethyl-3-cephem-4-carboxylate as a pale brown compound.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additionThe concentrate is introduced into a column
  3. washis eluted with 20% and 25% methanol solutions
  4. additionThe fractions containing the contemplated compound
  5. customare collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-497969b4483942d6bcf2b299d58c83dc
Source dataset
uspto-grants-1988_11
Patent number
US04786633

Reaction notes

Loading…