Acetone → cis 4-Fluoromethyl-3-[2-(2-tritylamino-4-thiazolyl)-2-trityloxyimino-acetamido]-2-oxo-azetidine

HRID 345652ノート

反応式

HRID 345652 の反応式
S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[C:12]([NH:31][C:32]1[S:33][CH:34]=[C:35]([C:37](=[N:41][O:42][C:43]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38](O)=[O:39])[N:36]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC(C)=O.Cl.[F:67][CH2:68][CH:69]1[NH:72][C:71](=[O:73])[CH:70]1[NH2:74]>C(Cl)Cl.C(N(CC)CC)C>[F:67][CH2:68][C@H:69]1[NH:72][C:71](=[O:73])[C@H:70]1[NH:74][C:38](=[O:39])[C:37]([C:35]1[N:36]=[C:32]([NH:31][C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[S:33][CH:34]=1)=[N:41][O:42][C:43]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)([C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

参加物

7

反応物 4

HCID 180AcetoneHCID 73974-Toluenesulfonyl chlorideHCID 53447342HCID 53447342、化合物HCID 679317054-Fluoromethyl-3-amino-2-oxo-azetidine hydrochloride

生成物 1

HCID 131716315cis 4-Fluoromethyl-3-[2-(2-tritylamino-4-thiazolyl)-2-trityloxyimino-acetamido]-2-oxo-azetidine

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒2 回

実験手順

0.228 g of tosyl chloride were added to a mixture of 0.806 g of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-trityloxyimino-acetic acid, 5 ml of acetone and 0.17 ml of triethylamine and the mixture was stirred for one hour. A solution of 0.155 g of 4-fluoromethyl-3-amino-2-oxo-azetidine hydrochloride in 5 ml of methylene chloride and 0.31 ml of triethylamine was added to the mixture which was stirred for 20 minutes and added to methylene chloride. The mixture was stirred for 90 minutes and was evaporated to dryness. The residue was added to methylene chloride and water with stirring and the decanted organic phase was dried and evaporated to dryness. The residue was chromatographed over silica gel and was eluted with ether to obtain 0.598 g of racemate of the syn isomer of cis 4-fluoromethyl-3-[2-(2-tritylamino-4-thiazolyl)-2-trityloxyimino-acetamido]-2-oxo-azetidine.

後処理

  1. stirringwas stirred for 20 minutes
  2. stirringThe mixture was stirred for 90 minutes
  3. customwas evaporated to dryness
  4. additionThe residue was added to methylene chloride and water
  5. stirringwith stirring
  6. customthe decanted organic phase was dried
  7. customevaporated to dryness
  8. customThe residue was chromatographed over silica gel
  9. washwas eluted with ether

出典と根拠

ORDレコード
ord-90d8a921fa5a4b9bae8ab1e4ec8ba383
出典データセット
uspto-grants-1991_10
特許番号
US05057512

反応ノート

読み込み中…