Pyridine → HCID 131717054, compound

HRID 346391Notes

Reaction equation

HRID 346391 reaction equation
I[CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:58])[C:29](=[N:55][O:56][CH3:57])[C:30]3[N:31]=[C:32]([NH:35][C:36]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[S:33][CH:34]=3)[C:25](=[O:59])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([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)=[O:10].[OH:60][C:61]1[CH:62]=[C:63]([C:68]2[S:72][C:71]([SH:73])=[N:70][N:69]=2)[CH:64]=[CH:65][C:66]=1[OH:67].[C:74](OC(=O)C)(=[O:76])[CH3:75].N1[CH:86]=[CH:85]C=CC=1.CN(C)C=[O:90]>>[C:74]([O:60][C:61]1[CH:62]=[C:63]([C:68]2[S:72][C:71]([S:73][CH2:2][C:3]3[CH2:4][S:5][C@@H:6]4[C@H:26]([NH:27][C:28](=[O:58])[C:29](=[N:55][O:56][CH3:57])[C:30]5[N:31]=[C:32]([NH:35][C:36]([C:49]6[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=6)([C:43]6[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=6)[C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=6)[S:33][CH:34]=5)[C:25](=[O:59])[N:7]4[C:8]=3[C:9]([O:11][CH:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])=[N:70][N:69]=2)[CH:64]=[CH:65][C:66]=1[O:67][C:85](=[O:90])[CH3:86])(=[O:76])[CH3:75]

Participants

6

Reactant 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 131717053HCID 131717053, compoundHCID 178515918HCID 178515918, compound

Product 1

HCID 131717054HCID 131717054, compoundYield 60%

Procedure

1.0 g (1.09 mmol) of benzhydryl 3-iodomethyl-7β-[2-metoxyimino-2-( 2-tritylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylate (syn-isomer) was dissolved in 10.0 ml of N,N-dimethylformamide, and 0.30 g (1.33 mmol) of 5-(3,4-dihydroxyphenyl)-2-mercapto-1,3,4-thiadiazole was added thereto. The mixture was stirred at room temperature for 2 hours. To the reaction solution 1.0 ml of acetic anhydride and 0.8 ml of pyridine were added and stirred at room temperature for 1 hour. The solvent was distilled. off under reduced pressure, and the residue was purified by silica gel cloumn chromatography (Wakogel C-300 ethyl acetate:hexane =3:1) to obtain 0.73 g (yield: 60%) of benzhydryl 3-[5-(3,4-diacetoxyphenyl)-1,3, 4-thiadiazol-2-yl]thiomethyl-7β-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl) acetamido]-3-cephem-4-carboxylate as a foamy substance.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. distillationThe solvent was distilled
  3. customoff under reduced pressure, and the residue was purified by silica gel cloumn chromatography (Wakogel C-300 ethyl acetate:hexane =3:1)

Sources & evidence

ORD record
ord-8dbbf7bc8cb34f46a867035d7c9f69ff
Source dataset
uspto-grants-1991_10
Patent number
US05061794

Reaction notes

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