Sodium Bicarbonate → HCID 178508521, compound

HRID 2253992Notes

Reaction equation

HRID 2253992 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:30]/[O:31][CH:32]([C:48]([O:50]C(C)(C)C)=[O:49])[S:33][C:34]2[CH:39]=[CH:38][C:37]([O:40]C(=O)C)=[C:36]([O:44]C(=O)C)[CH:35]=2)/[C:8]([NH:10][C@@H:11]2[C:28](=[O:29])[N:13]3[C:14]([C:25]([O-:27])=[O:26])=[C:15]([CH2:18][S:19][C:20]4[S:24][N:23]=[N:22][CH:21]=4)[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:30]/[O:31][CH:32]([C:48]([OH:50])=[O:49])[S:33][C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([OH:44])[CH:35]=2)/[C:8]([NH:10][C@@H:11]2[C:28](=[O:29])[N:13]3[C:14]([C:25]([O-:27])=[O:26])=[C:15]([CH2:18][S:19][C:20]4[S:24][N:23]=[N:22][CH:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+:59].[Na+:59].[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:30]/[O:31][CH:32]([S:33][C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([OH:44])[CH:35]=2)[C:48]([OH:50])=[O:49])/[C:8]([NH:10][C@@H:11]2[C:28](=[O:29])[N:13]3[C:14]([C:25]([O-:27])=[O:26])=[C:15]([CH2:18][S:19][C:20]4[S:24][N:23]=[N:22][CH:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178475463HCID 178475463, compound

Product 1

HCID 178508521HCID 178508521, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

950 mg of 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(R S)-(tert-butoxycarbonyl)(3,4-diacetoxyphenylthio)methoxy]imino]acetamido]-3-(1,2,3-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate obtained from Example 22 was suspended in 30 ml of water, and saturated sodium hydrogen carbonate aqueous solution was added therein at the room temperature in order to make pH 8. After stirring for 2.5 hrs. at the room temperature, the aqueous solution was adsorbed on Diaion HP-20 and was eluted with water-methanol. The fraction containing the desired product was collected, concentrated and then, lyophilized to give 419 mg of disodium 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(R S)-(carboxy)(3,4-dihydroxyphenylthio)methoxy]imino]acetamido]-3-(1,2,3-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate.

Workup

  1. customat the room temperature
  2. customat the room temperature
  3. washwas eluted with water-methanol
  4. additionThe fraction containing the desired product
  5. customwas collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-512e4acead4b4c8a87f3a539ae273f9e
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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