4-Toluenesulfonyl chloride → cis 4-Thiocyanatomethyl-3-[2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetamido]-2-oxo-azetidine

HRID 345651Notes

Reaction equation

HRID 345651 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][CH3:43])[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.Cl.[S:45]([CH2:48][C@H:49]1[NH:52][C:51](=[O:53])[C@H:50]1[NH2:54])[C:46]#[N:47]>C(Cl)Cl.C(N(CC)CC)C>[S:45]([CH2:48][C@H:49]1[NH:52][C:51](=[O:53])[C@H:50]1[NH:54][C:38](=[O:40])[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][CH3:43])[C:46]#[N:47]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 2724510(Z)-2-(2-Tritylaminothiazol-4-yl)-2-methoxyiminoacetic acidHCID 86743760cis 4-Thiocyanatomethyl-3-amino-2-oxo-azetidine hydrochloride

Product 1

HCID 86743762cis 4-Thiocyanatomethyl-3-[2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetamido]-2-oxo-azetidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

1 ml of triethylamine and then 1.38 g of tosyl chloride were added to a suspension of 3.19 g of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetic acid in 50 ml of methylene chloride and the mixture was stirred at room temperature for 40 minutes. A solution of 1.162 g of the product of Step C in 40 ml of methylene chloride and 2 ml of trietylamine were added to the mixture over 5 minutes and the mixture was stirred for 4 hours, was washed with water, then with water containing 4 ml of N hydrochloric acid, dried and evaporated to dryness. The residue was dissolved in ethyl acetate and the solution was iced and vacuum filtered. The product was washed with methanol and dried to obtain 0.709 g of racemate of syn isomer of cis 4-thiocyanatomethyl-3-[2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetamido]-2-oxo-azetidine. The mother liquors were evaporated to dryness and the residue was chromatographed over silica gel. Elution with a 93-7 chloroform-methanol mixture yielded another 1.069 g of the said product.

Workup

  1. stirringthe mixture was stirred for 4 hours
  2. washwas washed with water
  3. dry with materialwith water containing 4 ml of N hydrochloric acid, dried
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. filtrationvacuum filtered
  7. washThe product was washed with methanol
  8. customdried

Sources & evidence

ORD record
ord-08ddc29bafdc4d5cb3a33639e0282bc2
Source dataset
uspto-grants-1991_10
Patent number
US05057512

Reaction notes

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