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

HRID 345652Notes

Reaction equation

HRID 345652 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-90d8a921fa5a4b9bae8ab1e4ec8ba383
Source dataset
uspto-grants-1991_10
Patent number
US05057512

Reaction notes

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