Sulfuric Acid → 7-(5-(Chloroacetamido)-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

HRID 614639

Reaktionsgleichung

Reaktionsgleichung von HRID 614639
[NH2:1][CH:2]([C:26]([OH:28])=[O:27])[CH2:3][CH2:4][CH2:5][C:6]([NH:8][CH:9]1[C:24](=[O:25])[N:11]2[C:12]([C:21]([OH:23])=[O:22])=[C:13]([CH2:16][O:17][C:18](=[O:20])[NH2:19])[CH2:14][S:15][C@H:10]12)=[O:7].[Cl:29][CH2:30][C:31](Cl)=[O:32].[OH-].[Na+].S(=O)(=O)(O)O>B([O-])([O-])[O-].[Na+].[Na+].[Na+].C(OCC)(=O)C.C(O)C>[Cl:29][CH2:30][C:31]([NH:1][CH:2]([C:26]([OH:28])=[O:27])[CH2:3][CH2:4][CH2:5][C:6]([NH:8][CH:9]1[C:24](=[O:25])[N:11]2[C:12]([C:21]([OH:23])=[O:22])=[C:13]([CH2:16][O:17][C:18](=[O:20])[NH2:19])[CH2:14][S:15][C@H:10]12)=[O:7])=[O:32]

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 6577Chloroacetyl chloride2×HCID 14798Sodium HydroxideHCID 1297158037-(5-Amino-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

Produkt 1

HCID 1317114597-(5-(Chloroacetamido)-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 159383boric acid, sodium saltLösungsmittelHCID 21584252Ethanol ethylacetateLösungsmittel

Versuchsvorschrift

Five hundred milligrams of 7-(5-amino-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid was dissolved in 10 milliliters of sodium borate buffer and 650 milligrams of chloroacetyl chloride was added at ~20° C., keeping the pH of 9.0-9.5 by addition of 40 percent sodium hydroxide solution. After addition of the chloroacetyl chloride was complete, the reaction mixture was stirred for thirty minutes. The pH was adjusted to about 6.5 by addition of 30 percent sulfuric acid; then 10 milliliters of ethyl acetate:ethanol (9:1) was added, and the pH adjusted to 2.0. The organic layer was separated, dried over anhydrous magnesium sulfate, and ether was added, resulting in the precipitation of the desired 7-(5-(chloroacetamido)-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid. It was separated as a white powder, 195 milligrams, and characterized: titration (in 66 percent dimethylformamide): initial pH 3.9 pKa's at 4.8 and 6.1. Amino acid analysis: 0.12 μM./mg. of glycine and 1.9 μM./mg. of α-aminoadipic acid. NMR in dimethylsulfoxide-d6 showed bands at 6.36, 6.58 (2-CH2, q, J = 18); 5.08, 5.35 (3-CH2, q, J = 13); 4.89 (H-6, d, J= 5.0); 4.34 (H-7, q, J = 5.0, 8.0); 3.41 (CONH2, s); 5.87 (COCH2Cl, s); 1.17 τ (7-NH, d, J = 8.0 Hz).

Aufarbeitung

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate, and ether
  3. additionwas added

Quellen und Nachweise

ORD-Eintrag
ord-79c8abc36ea246e09a9957f432dc511c
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04145538

Verknüpfte Notizen

Wird geladen…