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

HRID 614639

반응식

HRID 614639 반응식
[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]

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 6577Chloroacetyl chloride2회HCID 14798Sodium HydroxideHCID 1297158037-(5-Amino-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

생성물 1

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

시약·촉매·용매 2

HCID 159383boric acid, sodium salt용매HCID 21584252Ethanol ethylacetate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-79c8abc36ea246e09a9957f432dc511c
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04145538

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