2,6-Lutidine → HCID 67859952, compound

HRID 1195569Notes

Reaction equation

HRID 1195569 reaction equation
Cl.[NH2:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:7]([CH:10]=[CH2:11])[CH2:8][S:9][C@H:4]12.N1C(C)=CC=CC=1C.[C:38]([NH:57][C:58]1[S:62][C:61]([CH2:63][C:64](O)=[O:65])=[N:60][N:59]=1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.O.O1CCCC1.C(OCC)(=O)C.CN(C)C=O>[C:38]([NH:57][C:58]1[S:62][C:61]([CH2:63][C:64]([NH:2][CH:3]2[C:28](=[O:29])[N:5]3[C:6]([C:12]([O:14][CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[O:13])=[C:7]([CH:10]=[CH2:11])[CH2:8][S:9][C@H:4]23)=[O:65])=[N:60][N:59]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

10

Reactant 4

HCID 79372,6-LutidineHCID 10868DicyclohexylcarbodiimideHCID 12818005Benzhydryl 7-amino-3vinyl-3cephem-4-carboxylate hydrochlorideHCID 19790156HCID 19790156, compound

Product 1

HCID 67859952HCID 67859952, compoundYield 66.8%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of benzhydryl 7-amino-3-vinyl-3-cephem-4- carboxylate monohydrochloride (2.15 g) in methylene chloride (100 ml) was added 2,6- lutidine (0.54 g) under ice-cooling. To the resultant solution were added 2-(5-tritylamino-1,3,4- thiadiazol-2- yl)-acetic acid (2,4 g), N,N'-dicyclohexylcarbodiimide (1.03 g), tetrahydrofuran (200 ml) and N,N-dimethylformamide (60 ml), and the mixture was stirred at ambient temperature for a day. Removal of the solvent gave a residue, to which a mixed solvent of ethyl acetate, tetrahydrofuran and water was added. The insoluble substances were removed by filtration, and the filtrate was washed with dilute hydrochloric acid, a saturated aqueous sodium bicarbonate and an aqueous sodium chloride, followed by drying over magnesium sulfate. Removal of the solvent gave a residue, which was washed with diisopropyl ether to obtain benzhydryl 7-[2-(5-tritylamino-1,3,4- thiadiazol-2-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (2.6 g).

Workup

  1. temperaturecooling
  2. customRemoval of the solvent
  3. customgave a residue
  4. customThe insoluble substances were removed by filtration
  5. washthe filtrate was washed with dilute hydrochloric acid
  6. dry with materialby drying over magnesium sulfate
  7. customRemoval of the solvent
  8. customgave a residue, which
  9. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-027c0ade8b6341e39f77be7731bb812d
Source dataset
uspto-grants-1992_05
Patent number
US05110921

Reaction notes

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