Potassium Carbonate → HCID 131714366, compound

HRID 980989Notes

Reaction equation

HRID 980989 reaction equation
Cl.[I-].[CH:3]([O:16][C:17]([C:19]1[N:24]2[C:25](=[O:28])[CH:26]([NH2:27])[C@H:23]2[S:22][CH2:21][C:20]=1[CH2:29][P+:30]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:18])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)(O)[O-].[Na+].Cl.[NH2:55][C:56]1[S:60][N:59]=[C:58]([C:61](=[N:65][O:66][CH2:67][CH3:68])[C:62](Cl)=[O:63])[N:57]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[NH2:55][C:56]1[S:60][N:59]=[C:58]([C:61](=[N:65][O:66][CH2:67][CH3:68])[C:62]([NH:27][CH:26]2[C:25](=[O:28])[N:24]3[C:19]([C:17]([O:16][CH:3]([C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=4)[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)=[O:18])=[C:20]([CH:29]=[P:30]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH2:21][S:22][C@H:23]23)=[O:63])[N:57]=1

Participants

7

Reactant 4

HCID 11430Potassium Carbonate2×HCID 516892Sodium BicarbonateHCID 867392542-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochlorideHCID 88625133(4-Benzhydryloxycarbonyl-7-amino-3-cephem-3-ylmethyl)triphenylphosphonium iodide hydrochloride

Product 1

HCID 131714366HCID 131714366, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

(4-benzhydryloxycarbonyl-7-amino-3-cephem-3-ylmethyl)triphenylphosphonium iodide hydrochloride (5 g) was dissolved in a mixed solution of tetrahydrofuran (35 ml) and 35 ml of aqueous sodium bicarbonate (1.6 g). To the solution was added a solution of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyimino acetylchloride hydrochloride (syn isomer)(2.6 g) in tetrahydrofuran at -3° C. to 3° C., and the solution was stirred for 30 minutes under keeping the pH 6.5 to 7.5 with 20% aqueous potassium carbonate. Ethyl acetate was added to the reaction mixture and the mixture was adjusted to pH 10.0 with 20% aqueous potassium carbonate. The separated organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated to give benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-(triphenylphosphoranediylmethyl)-3-cephem-4-carboxylate (syn isomer)(4.5 g).

Workup

  1. washThe separated organic layer was washed with saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-2c710f4907f54474b4f2eed6994cfc04
Source dataset
uspto-grants-1987_01
Patent number
US04639448

Reaction notes

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