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

HRID 1199591
Notes
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Reaction equation

HRID 1199591 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-ce86a4cacb794e2eb22e4b9c61eee449
Source dataset
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04900728

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes