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

HRID 614639

反応式

HRID 614639 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 159383boric acid, sodium salt溶媒HCID 21584252Ethanol ethylacetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-79c8abc36ea246e09a9957f432dc511c
出典データセット
uspto-grants-1979_03
特許番号
US04145538

関連ノート

読み込み中…