Phosphorus oxychloride → HCID 86738683, compound

HRID 1902519Notes

Reaction equation

HRID 1902519 reaction equation
P(Cl)(Cl)(Cl)=O.C[Si](CC(N)=O)(C)C.[NH2:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:24][O:25][CH3:26])[C:21]([OH:23])=O)[N:19]=1.[NH2:27][CH:28]1[C:53](=[O:54])[N:30]2[CH:31]([C:40]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][CH:45]=3)=[O:41])[C:32](=[CH:35][O:36][C:37](=[O:39])[CH3:38])[CH2:33][S:34][C@H:29]12.C(=O)(O)[O-].[Na+]>O1CCCC1.O.C(OCC)(=O)C.CN(C)C=O>[NH2:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:24][O:25][CH3:26])[C:21]([NH:27][CH:28]2[C:53](=[O:54])[N:30]3[CH:31]([C:40]([O:42][CH2:43][C:44]4[CH:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][CH:45]=4)=[O:41])[C:32](=[CH:35][O:36][C:37](=[O:39])[CH3:38])[CH2:33][S:34][C@H:29]23)=[O:23])[N:19]=1

Participants

10

Reactant 5

HCID 24813Phosphorus oxychlorideHCID 1252162-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acidHCID 357676Acetamide, 2-(trimethylsilyl)-2×HCID 516892Sodium BicarbonateHCID 70524728HCID 70524728, compound

Product 1

HCID 86738683HCID 86738683, compoundYield 64.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Phosphorus oxychloride (1.7 g.), trimethylsilylacetamide (1 g.) and N,N-dimethylformamide (0.73 g.) were added to a suspension of 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 1.8 g.) in tetrahydrofuran (20 ml.) at 5° C. Thus obtained solution was added all at once to a solution of 4-nitrobenzyl 7-amino-3-acetoxymethylenecepham-4-carboxylate (2.9 g.) and trimethylsilylacetamide (5.4 g.) in tetrahydrofuran (30 ml) at -20° C., and the mixed solution was stirred at -10° to -15° C. for an hour. After adding water (10 ml.) at -30° C., the resultant mixture was poured into a solution of ethyl acetate (200 ml) and water (200 ml.), and adjusted to pH 7.5 with sodium bicarbonate. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride and treated with activated charcoal. After concentrating the solution under reduced pressure, the residue was pulverized with diisopropyl ether and collected by filtration to give 4-nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-acetoxymethylenecepham-4-carboxylate (syn isomer, 2.7 g.).

Workup

  1. customThe organic layer was separated
  2. washwashed with a saturated aqueous solution of sodium chloride
  3. additiontreated with activated charcoal
  4. concentrationAfter concentrating the solution under reduced pressure
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-4e403d1f0caf4f58b99cff422757aed9
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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