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

HRID 1199590Notes

Reaction equation

HRID 1199590 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][CH:43]([F:45])[F:44])[C:38]([OH:40])=O)[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:51][CH2:52][C@H:53]1[NH:56][C:55](=[O:57])[C@H:54]1[NH2:58]>C(N(CC)CC)C.C(Cl)Cl>[F:51][CH2:52][C@H:53]1[NH:56][C:55](=[O:57])[C@H:54]1[NH:58][C:38](=[O:40])[C:37]([C:35]1[N:36]=[C:32]([NH:31][C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[S:33][CH:34]=1)=[N:41][O:42][CH:43]([F:45])[F:44]

Participants

7

Reactant 4

HCID 180AcetoneHCID 73974-Toluenesulfonyl chlorideHCID 13244798cis 4-Fluoromethyl-3-amino-2-oxo-azetidine hydrochlorideHCID 536668022-(2-Tritylamino-4-thiazolyl)-2-difluoromethoxyimino-acetic acid

Product 1

HCID 86743763cis 4-Fluoromethyl-3-[2-(2-tritylamino-4-thiazolyl)-2-difluoromethoxyimino-acetamido]-2-oxo-azetidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

0.339 g of tosyl chloride were added to a mixture of 0.914 g of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-difluoromethoxyimino-acetic acid, 7 ml of acetone and 0.25 ml of trietylamine and the mixture was stirred for 50 minutes after which a solution of 0.23 g of cis 4-fluoromethyl-3-amino-2-oxo-azetidine hydrochloride, 7 ml of methylene chloride and 0.45 ml of triethylamine was added thereto. The mixture was stirred for 90 minutes and was evaporated to dryness. The residue was added to methylene chloride and water and then 3 ml of 10% sodium bicarbonate solution. The mixture was stirred and the decanted aqueous phase was extracted with methylene chloride. The combined organic phases were dried and evaporated to dryness. The residue was taken up in ethanol and the solution was cooled and vacuum filtered. The crystals were rinsed with ethanol, then with ether and dried to obtain 0.537 g of racemate of the syn isomer of cis 4-fluoromethyl-3-[2-(2-tritylamino-4-thiazolyl)-2-difluoromethoxyimino-acetamido]-2-oxo-azetidine. STEP B: Racemate of the syn isomer of cis 4-fluoromethyl-3-[2-(2-amino-4-thiazolyl)-2-difluoromethoxyimino-acetamido]-2-oxo-azetidine-1-sulfonic acid

Workup

  1. additionwas added
  2. customwas evaporated to dryness
  3. additionThe residue was added to methylene chloride and water
  4. stirringThe mixture was stirred
  5. extractionthe decanted aqueous phase was extracted with methylene chloride
  6. customThe combined organic phases were dried
  7. customevaporated to dryness
  8. temperaturethe solution was cooled
  9. filtrationvacuum filtered
  10. washThe crystals were rinsed with ethanol
  11. dry with materialwith ether and dried

Sources & evidence

ORD record
ord-1acac33dcd0a4d52914ac3d750b59667
Source dataset
uspto-grants-1990_02
Patent number
US04900728

Reaction notes

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