Sodium Bicarbonate → HCID 178508522, compound

HRID 2253982Notes

Reaction equation

HRID 2253982 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:34]/[O:35][CH:36]([C:52]([OH:54])=[O:53])[S:37][C:38]2[CH:43]=[CH:42][C:41]([O:44]C(=O)C)=[C:40]([O:48]C(=O)C)[CH:39]=2)/[C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:29]([OH:31])=[O:30])=[C:15]([CH2:18][S:19][C:20]4[S:24][N:23]=[C:22]([OH:25])[C:21]=4[C:26]([OH:28])=[O:27])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(=O)([O-])O.[Na+:59]>O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:34]/[O:35][CH:36]([C:52]([OH:54])=[O:53])[S:37][C:38]2[CH:43]=[CH:42][C:41]([OH:44])=[C:40]([OH:48])[CH:39]=2)/[C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:29]([O-:31])=[O:30])=[C:15]([CH2:18][S:19][C:20]4[S:24][N:23]=[C:22]([OH:25])[C:21]=4[C:26]([OH:28])=[O:27])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+:59].[Na+:59].[Na+:59].[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:34]/[O:35][CH:36]([S:37][C:38]2[CH:43]=[CH:42][C:41]([OH:44])=[C:40]([OH:48])[CH:39]=2)[C:52]([OH:54])=[O:53])/[C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:29]([O-:31])=[O:30])=[C:15]([CH2:18][S:19][C:20]4[S:24][N:23]=[C:22]([OH:25])[C:21]=4[C:26]([OH:28])=[O:27])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:34]/[O:35][CH:36]([S:37][C:38]2[CH:43]=[CH:42][C:41]([OH:44])=[C:40]([OH:48])[CH:39]=2)[C:52]([OH:54])=[O:53])/[C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:29]([O-:31])=[O:30])=[C:15]([CH2:18][S:19][C:20]4[S:24][N:23]=[C:22]([OH:25])[C:21]=4[C:26]([OH:28])=[O:27])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178475465HCID 178475465, compound

Product 1

HCID 178508522HCID 178508522, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 600 mg of 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(R S)-(carboxy)(3,4-diacetoxyphenylthio)methoxy]imino]acetamido]-3-[[(4-carboxy-3-hydroxy-5-isothiazolyl)thio]methyl]-3-cephem-4-carboxylic acid obtained in Example 4 (10) was suspended in 20 ml of water, saturated sodium hydrogencarbonate aqueous solution was added to the suspension at room temperature to adjust pH to 8. After stirring at room temperature for 2.5 hours, the aqueous solution was adsorbed to DIAION HP20 followed by elution with water. The fractions containing the desired product were collected. After concentration, the concentrate was freeze dried to give 150 mg of trisodium 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(R S)-(carboxy)(3,4-dihydroxyphenylthio)methoxy]imino]acetamido]-3-[[(4-carboxy-3-hydroxy-5-isothiazolyl)thio]methyl]-3-cephem-4-carboxylate.

Workup

  1. washfollowed by elution with water
  2. additionThe fractions containing the desired product
  3. customwere collected
  4. concentrationAfter concentration
  5. customdried

Sources & evidence

ORD record
ord-0a982adc99764d9ea4f05777ee2dc6d5
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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