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

HRID 345652노트

반응식

HRID 345652 반응식
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

참가 물질

7

반응물 4

HCID 180AcetoneHCID 73974-Toluenesulfonyl chlorideHCID 53447342HCID 53447342, 화합물HCID 679317054-Fluoromethyl-3-amino-2-oxo-azetidine hydrochloride

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-90d8a921fa5a4b9bae8ab1e4ec8ba383
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05057512

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