Sodium Bicarbonate → HCID 131712861, compound

HRID 2198536Notes

Reaction equation

HRID 2198536 reaction equation
[NH:1]=[C:2]1[N:6]([OH:7])[C:5]([C:8](=[N:29][O:30][CH3:31])[C:9]([NH:11][C@@H:12]2[C:27](=[O:28])[N:14]3[C:15]([C:24]([OH:26])=[O:25])=[C:16]([CH2:19]OC(=O)C)[CH2:17][S:18][C@H:13]23)=[O:10])=[CH:4][S:3]1.O.O.[Na].[CH3:35][N:36]1[C:40]([SH:41])=[N:39][N:38]=[N:37]1.C([O-])(O)=O.[Na+]>O.Cl.C(O)=O.CO.C(Cl)(Cl)Cl>[NH:1]=[C:2]1[N:6]([OH:7])[C:5]([C:8](=[N:29][O:30][CH3:31])[C:9]([NH:11][C@@H:12]2[C:27](=[O:28])[N:14]3[C:15]([C:24]([OH:26])=[O:25])=[C:16]([CH2:19][S:41][C:40]4[N:36]([CH3:35])[N:37]=[N:38][N:39]=4)[CH2:17][S:18][C@H:13]23)=[O:10])=[CH:4][S:3]1

Participants

9

Reactant 3

HCID 516892Sodium BicarbonateHCID 131712862HCID 131712862, compoundHCID 178482032HCID 178482032, compound

Product 1

HCID 131712861HCID 131712861, compoundYield 77.5%

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidCatalystHCID 284Formic AcidSolvent2×HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Conditions

Temperature
67 °C

Procedure

To a mixture of 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxyimino-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (prepared as described in example 1) (120 mg), and 1-methyl-5 mercapto-1,2,3,4-tetrazole sodium salt di-hydrate, (30 mg), in distilled water (7.5 ml), NaHCO3 was added in small portions with stirring, until a clear solution was obtained and a pH value of 6.5-7 was reached. This solution was heated for 6.5 hours in an oil bath at 67° C.; the progress of the reaction can be monitored by TLC (three-days-old CHCl3 160/MeOH 70/HCOOH 30 or freshly prepared CHCl3 160/MeOH 10/HCOOH 30 phases; the product has a slightly lower Rf value than the starting material). After cooling at 5° C., a few drops of 8% HCl were carefully added under stirring, causing the separation of a precipitate (at about pH 3). This was collected, washed with acetone (in order to remove excess 1-methyl-5-mercapto-1,2,3,4-tetrazole) and dried, thus giving 70 mg of the title compound, which was identical to that prepared in example 2.

Workup

  1. customwas obtained
  2. customthe progress of the reaction
  3. temperatureAfter cooling at 5° C.
  4. stirringunder stirring
  5. customthe separation of a precipitate (at about pH 3)
  6. customThis was collected
  7. washwashed with acetone (in order to remove excess 1-methyl-5-mercapto-1,2,3,4-tetrazole)
  8. customdried

Sources & evidence

ORD record
ord-b5a5338a33f3432c96e5c2a631331fb4
Source dataset
uspto-grants-1982_11
Patent number
US04358448

Reaction notes

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