Thiourea → 7beta-[alpha-ethoxyimino-(2-aminothiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester

HRID 866444

Reaktionsgleichung

Reaktionsgleichung von HRID 866444
[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:43])[C@@H:24]([NH:25][C:26](=[O:42])[C:27]([C:32]3[N:33]=[C:34]([NH:37]C(=O)CCl)[S:35][CH:36]=3)=[N:28][O:29][CH2:30][CH3:31])[C@H:21]2[S:20][CH2:19][C:18]=1[CH:44]([S:46][C:47]1[NH:51][N:50]=[N:49][N:48]=1)[CH3:45])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC(N)=S>O1CCCC1.C(O)C.[Br-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:43])[C@@H:24]([NH:25][C:26](=[O:42])[C:27](=[N:28][O:29][CH2:30][CH3:31])[C:32]3[N:33]=[C:34]([NH2:37])[S:35][CH:36]=3)[C@H:21]2[S:20][CH2:19][C:18]=1[CH:44]([S:46][C:47]1[NH:51][N:50]=[N:49][N:48]=1)[CH3:45])=[O:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 2

HCID 2723790ThioureaHCID 1784749067beta-{alpha-ethoxyimino-[2-(chloroacetamido)thiazol-4-yl]acetamido}-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester

Produkt 1

HCID 1784749077beta-[alpha-ethoxyimino-(2-aminothiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl esterAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 165294Benzyltriethylammonium bromideKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2.2 g of 7β-{α-ethoxyimino-[2-(chloroacetamido)thiazol-4-yl]acetamido}-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester in 20 ml of tetrahydrofuran is added a solution of 550 mg of thiourea in 20 ml of ethanol, followed by addition of 50 mg of triethylbenzylammonium bromide. The mixture is stirred for 20 hours at room temperature and concentrated. The residue is dissolved in a mixture of ethyl acetate and tetrahydrofuran and the solution was washed with aq. sodium bicarbonate solution and then water, followed by drying over anhydrous magnesium sulfate. The dried solution is subjected to distillation of the solvent to give powder which is washed with chloroform and ether and dried. The procedure yields 1.047 g of 7β-[β-ethoxyimino-(2-aminothiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester. Yield 52.9%.

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in a mixture of ethyl acetate and tetrahydrofuran
  3. washthe solution was washed with aq. sodium bicarbonate solution
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationThe dried solution is subjected to distillation of the solvent
  6. customto give powder which
  7. washis washed with chloroform and ether
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ddb67a883e454a55b38979dcd7181003
Quelldatensatz
uspto-grants-1978_07
Patentnummer
US04098888

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