Water → Sulbactam

HRID 224786

反応式

HRID 224786 の反応式
[Mn]([O-])(=O)(=O)=[O:2].[K+].[Na].[CH3:8][C:9]1([CH3:20])[S:13][C@@H:12]2[CH2:14][C:15](=[O:16])[N:11]2[C@H:10]1[C:17]([OH:19])=[O:18].[OH2:21]>C(O)(=O)C>[CH3:8][C:9]1([CH3:20])[S:13](=[O:2])(=[O:21])[C@@H:12]2[CH2:14][C:15](=[O:16])[N:11]2[C@H:10]1[C:17]([OH:19])=[O:18]

参加物

6

反応物 4

HCID 962Water2 回HCID 6891Penicillanic AcidHCID 516875Potassium PermanganateHCID 5360545Sodium

生成物 1

HCID 130313Sulbactam収率 78%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
5 °C

実験手順

To a solution of 6.51 g. (41 mmole) of potassium permanganate in 130 ml. of water and 4.95 ml. of glacial acetic acid, cooled to ca. 5° C., was added a cold (ca. 5° C.) solution of 4.58 g. (21 mmole) of the sodium salt of penicillanic acid in 50 ml. of water. The mixture was stirred at ca. 5° C. for 20 minutes and then the cooling bath was removed. Solid sodium bisulfite was added until the color of the potassium permanganate had been discharged, and then the mixture was filtered. To the aqueous filtrate was added half its volume of saturated sodium chloride solution, and then the pH was adjusted to 1.7. The acidic solution was extracted with ethyl acetate. The extracts were dried, and then evaporated in vacuo, to give 3.47 g. of the title product. The aqueous mother liquor was saturated with sodium chloride, and further extracted with ethyl acetate. The ethyl acetate solution was dried and evaporated in vacuo, to give a further 0.28 g. of product. The total yield was therefore 3.75 g. (78% yield). The NMR spectrum (DMSO-d6) of the product showed absorptions at 1.40 (s,3H), 1.50 (s,3H), 3.13 (d of d's, 1H, J1 =16 Hz, J2 =2 Hz), 3.63 (d of d's, 1H, J1 =16 Hz, J2 =4 Hz), 4.22 (s, 1H) and 5.03 (d of d's, 1H, J1 =4 Hz, J2 =2 Hz) ppm.

後処理

  1. additionwas added a cold (ca. 5° C.) solution of 4.58 g
  2. customthe cooling bath was removed
  3. additionSolid sodium bisulfite was added until the color of the potassium permanganate
  4. filtrationthe mixture was filtered
  5. additionTo the aqueous filtrate was added half its volume of saturated sodium chloride solution
  6. extractionThe acidic solution was extracted with ethyl acetate
  7. customThe extracts were dried
  8. customevaporated in vacuo
  9. customto give 3.47 g

出典と根拠

ORDレコード
ord-2df09b1aa91241f3acc27b1ba1411757
出典データセット
uspto-grants-1980_11
特許番号
US04234579

関連ノート

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