Pyridine → (trans)-3-t-Butoxycarbonylamino-4-ethyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt

HRID 371222

反応式

HRID 371222 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](C)(C)[O:9][S:10](Cl)(=[O:12])=[O:11].[C:16]([O:20][C:21]([NH:23][C@H:24]1[C@H:27]([CH2:28][CH3:29])[NH:26][C:25]1=[O:30])=[O:22])([CH3:19])([CH3:18])[CH3:17].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>ClCCl.O>[CH2:25]([N+:1]([CH2:2][CH2:17][CH2:16][CH3:18])([CH2:6][CH2:5][CH2:4][CH3:3])[CH2:29][CH2:28][CH2:27][CH3:24])[CH2:24][CH2:27][CH3:28].[C:16]([O:20][C:21]([NH:23][C@H:24]1[C@H:27]([CH2:28][CH3:29])[N:26]([S:10]([O-:9])(=[O:12])=[O:11])[C:25]1=[O:30])=[O:22])([CH3:19])([CH3:18])[CH3:17]

参加物

7

反応物 4

HCID 1049Pyridine2 回HCID 62657Potassium Phosphate, Tribasic2 回HCID 78059Trimethylsilyl chlorosulphateHCID 70415750(trans)-3-t-Butoxycarbonylamino-4-ethyl-2-azetidinone

生成物 1

HCID 131714274(trans)-3-t-Butoxycarbonylamino-4-ethyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To 2 ml of absolute pyridine in 20 ml of dry dichloromethane is added trimethylsilyloxysulfonyl chloride (3.7 ml) in 5 ml of dry dichloromethane. The addition is accomplished at -30° C., under nitrogen, over a 10 minute period. After stirring at ambient temperature for 30 minutes, the flask is evacuated to yield a pyridine-sulfur trioxide complex. (trans)-3-t-Butoxycarbonylamino-4-ethyl-2-azetidinone (2.67 g) and 20 ml of dry pyridine are added to the flask which is then placed in an oil bath preheated to 90° C. After 15 minutes a clear solution is obtained and poured into 200 ml of a 1M solution of dibasic potassium phosphate. After the addition of 27 g of dibasic potassium phosphate and 100 ml of water a clear solution is obtained. The solution is extracted with two 60 ml portions of ethyl acetate. Tetrabutylammonium hydrogensulfate is added to the aqueous layer, and the aqueous solution is extracted with three 100 ml portions of dichloromethane and the combined organic layers are dried over MgSO4. Concentration in vacuo yields 6.9 g of the title compound.

後処理

  1. additionThe addition
  2. customthe flask is evacuated
  3. customto yield a pyridine-sulfur trioxide complex
  4. customis then placed in an oil bath
  5. custompreheated to 90° C
  6. customAfter 15 minutes a clear solution is obtained
  7. customis obtained
  8. extractionThe solution is extracted with two 60 ml portions of ethyl acetate
  9. additionTetrabutylammonium hydrogensulfate is added to the aqueous layer
  10. extractionthe aqueous solution is extracted with three 100 ml portions of dichloromethane
  11. dry with materialthe combined organic layers are dried over MgSO4
  12. concentrationConcentration in vacuo

出典と根拠

ORDレコード
ord-e7759c7f61bc4cdab10a391d49e33250
出典データセット
uspto-grants-1985_07
特許番号
US04529698

関連ノート

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