Phosphorus oxychloride → HCID 14799591, compound

HRID 974122Notes

Reaction equation

HRID 974122 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([NH:25][C:26]1[S:30][N:29]=[C:28](/[C:31](=[N:35]/[O:36][CH2:37][C:38]([F:41])([F:40])[F:39])/[C:32](O)=[O:33])[N:27]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.[NH2:43][C@@H:44]1[C:67](=[O:68])[N:46]2[C:47]([C:55]([O:57][CH2:58][C:59]3[CH:64]=[CH:63][C:62]([O:65][CH3:66])=[CH:61][CH:60]=3)=[O:56])=[C:48](/[CH:51]=[CH:52]\[CH2:53][Cl:54])[CH2:49][S:50][C@H:45]12.C[Si](C)(C)NC(=O)C>C(OCC)(=O)C.O1CCCC1.CN(C)C=O>[C:6]([NH:25][C:26]1[S:30][N:29]=[C:28](/[C:31](=[N:35]/[O:36][CH2:37][C:38]([F:39])([F:41])[F:40])/[C:32]([NH:43][C@@H:44]2[C:67](=[O:68])[N:46]3[C:47]([C:55]([O:57][CH2:58][C:59]4[CH:60]=[CH:61][C:62]([O:65][CH3:66])=[CH:63][CH:64]=4)=[O:56])=[C:48](/[CH:51]=[CH:52]\[CH2:53][Cl:54])[CH2:49][S:50][C@H:45]23)=[O:33])[N:27]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 25989Acetamide, N-(trimethylsilyl)-HCID 14799588HCID 14799588, compoundHCID 70101812HCID 70101812, compound

Product 1

HCID 14799591HCID 14799591, compoundYield 60.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
-20 °C

Procedure

A mixture solution comprising dimethylformamide (0.247 ml) and tetrahydrofuran (3 ml) was cooled to -10° C., and phosphorus oxychloride (0.297 ml) was added thereto and stirred for 40 minutes with ice-cooling. To the resulting solution was added the tetrahydrofuran solution (4 ml) of 2-(5-tritylamino-1,2,4-thiadiazol-3-yl)-(Z)-2-(2,2,2-trifluoroethyl)oxyiminoacetic acid (1.36 g), followed by stirring for further one hour at the said temperature. The resulting reaction solution was added to a mixture solution comprising p-methoxybenzyl 7β-amino-3-[(Z)-3-chloro-1-propen-1-yl]-3-cephem-4-carboxylate hydrochloride (1.145 g), N-(trimethylsilyl)acetamide (2.09 g) and ethyl acetate (10 ml), with cooling at -20° C., followed by elevating the temperature up to 0° C. with stirring for one hour. After ethyl acetate was added to the reaction solution, this was washed with water and dried with anhydrous sodium sulfate. The solvent was evaporated out and the residue was purified by silicagel column chromatography to obtain the desired product (1.43 g).

Workup

  1. temperaturecooling
  2. stirringby stirring for further one hour at the said temperature
  3. customThe resulting reaction solution
  4. customup to 0° C.
  5. stirringwith stirring for one hour
  6. washthis was washed with water
  7. dry with materialdried with anhydrous sodium sulfate
  8. customThe solvent was evaporated out
  9. customthe residue was purified by silicagel column chromatography

Sources & evidence

ORD record
ord-4d42f8c7c417411192ce160dde093522
Source dataset
uspto-grants-1991_11
Patent number
US05066812

Reaction notes

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