Pyridine → HCID 131715962, compound

HRID 1904648Notes

Reaction equation

HRID 1904648 reaction equation
C(OC[O:9][C:10]([C:12]1[N:17]2[C:18](=[O:21])[CH:19]([NH2:20])[C@H:16]2[S:15][CH2:14][C:13]=1[CH:22]=[CH:23][C:24]1[S:28][CH:27]=[N:26][C:25]=1[CH3:29])=[O:11])(=O)C(C)(C)C.[C:30]([NH:49][C:50]1[S:51][CH:52]=[C:53]([C:55](=[N:59][O:60][CH3:61])[C:56](O)=[O:57])[N:54]=1)([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.N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>C(Cl)Cl.C(OCC)(=O)C>[CH3:61][O:60][N:59]=[C:55]([C:53]1[N:54]=[C:50]([NH:49][C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[S:51][CH:52]=1)[C:56]([NH:20][CH:19]1[C:18](=[O:21])[N:17]2[C:12]([C:10]([OH:9])=[O:11])=[C:13]([CH:22]=[CH:23][C:24]3[S:28][CH:27]=[N:26][C:25]=3[CH3:29])[CH2:14][S:15][C@H:16]12)=[O:57]

Participants

7

Reactant 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 2724510(Z)-2-(2-Tritylaminothiazol-4-yl)-2-methoxyiminoacetic acidHCID 131715963HCID 131715963, compound

Product 1

HCID 131715962HCID 131715962, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

7-Amino-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid pivaloyloxymethyl ester (0.229 g) as prepared in Reference Example 1 above was dissolved in methylene chloride (5 ml). The resultant solution was admixed with 2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetic acid (syn-isomer) (0.235 g) and methylene chloride (5 ml). To the mixture obtained were further added pyridine (0.07 ml) and then dropwise phosphorus oxychloride (0.07 ml) at -20° C. The reaction mixture was stirred for 10 minutes at 0° C. and poured into a mixture of ice-water (50 ml) and ethyl acetate (50 ml). After stirring, the organic phase was separated from the aqueous phase and washed with ice-wated and then with ice-cooled aqueous saturated sodium hydrogen carbonate solution. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified chromatographically on a column of silica gel (Wako gel C-300) (20 g ) as developed with benzene-ethyl acetate (5:1) as the development solvent. 7-[2-Methoxyimino-2(2-tritylaminothiazol-4yl)acetamido]-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid (syn-isomer) pivaloyloxymethyl ester (0.184 g) was obtained.

Workup

  1. customTo the mixture obtained
  2. customat -20° C
  3. stirringAfter stirring
  4. customthe organic phase was separated from the aqueous phase
  5. washwashed with ice-wated
  6. temperaturewith ice-cooled aqueous saturated sodium hydrogen carbonate solution
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified chromatographically on a column of silica gel (Wako gel C-300) (20 g )

Sources & evidence

ORD record
ord-166f6598dd8e4a679ebd59ce0c34ee42
Source dataset
uspto-grants-1989_06
Patent number
US04839350

Reaction notes

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