Sodium Carbonate → HCID 131712317, compound

HRID 894763Notes

Reaction equation

HRID 894763 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]([OH:12])=O)[N:8]=1)=[O:2].P(Cl)(Cl)(Cl)=O.[NH2:28][CH:29]1[C:49](=[O:50])[N:31]2[C:32]([C:36]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=3)=[O:37])=[CH:33][CH2:34][S:35][C@H:30]12.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.CC(C)=O.CN(C)C=O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]([NH:28][CH:29]2[C:49](=[O:50])[N:31]3[C:32]([C:36]([O:38][CH2:39][C:40]4[CH:41]=[CH:42][C:43]([N+:46]([O-:48])=[O:47])=[CH:44][CH:45]=4)=[O:37])=[CH:33][CH2:34][S:35][C@H:30]23)=[O:12])[N:8]=1)=[O:2]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 12775080p-Nitrobenzyl 7-amino-3-cephem-4-carboxylateHCID 543909512-t-Butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid

Product 1

HCID 131712317HCID 131712317, compoundYield 103.9%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-(2-Formamidothiazol-4-yl)-2-t-butoxycarbonylmethoxyiminoacetic acid (syn isomer, 5 g.), N,N-dimethylformamide (1.68 g.), phosphoryl chloride (3.52 g.) and tetrahydrofuran (50 ml.) were treated in a similar manner to that of Example 1-(1) to give an activated acid solution. The solution was added to a stined suspension of 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (5.23 g.), in tetrahydrofuran (26 ml.), acetone (13 ml.) and water (13 ml.) at -5° to 0° C., and stirred at the same temperature for 30 minutes while keeping at pH 7 to 7.5 with 20% aqueous solution of sodium carbonate. After removing the insoluble substance from the resultant mixture, the filtrate was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solution was concentrated in vacuo, and the residue was triturated with diethyl ether. The precipitates were collected by filtration and dried to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-t-butoxycarbonylmethoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 10.2 g.)

Workup

  1. customto give an activated acid solution
  2. customAfter removing the insoluble substance from the resultant mixture
  3. washthe filtrate was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution was concentrated in vacuo
  6. customthe residue was triturated with diethyl ether
  7. filtrationThe precipitates were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-e7f3f51ec689475d928530ffcb9bcb45
Source dataset
uspto-grants-1981_08
Patent number
US04284631

Reaction notes

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