4-Toluenesulfonyl chloride → HCID 131720175, compound

HRID 1376844Notes

Reaction equation

HRID 1376844 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH2:32][CH3:33])[C:27](O)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[NH2:45][C@H:46]1[C:53](=[O:54])[N:52]2[C@@H:47]1[CH2:48][S:49][C:50]([CH2:62][OH:63])=[C:51]2[C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56].C(=O)(O)[O-].[Na+]>CC(C)=O.O.C(N(CC)CC)C>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH2:32][CH3:33])[C:27]([NH:45][C@H:46]2[C:53](=[O:54])[N:52]3[C@@H:47]2[CH2:48][S:49][C:50]([CH2:62][OH:63])=[C:51]3[C:55]([O:57][C:58]([CH3:59])([CH3:60])[CH3:61])=[O:56])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 54056605HCID 54056605, compoundHCID 131720176HCID 131720176, compound

Product 1

HCID 131720175HCID 131720175, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

549 mg of the syn isomer of 2-[2-tritylaminothiazol-4-yl]-2-ethoxyimino acetic acid were dissolved in 5.5 ml of acetone and 0.18 ml of triethylamine and 228 mg of tosyl chloride were added immediately with stirring for 45 minutes. A solution of 285 mg of the product of Step C in 1 ml of water, 1.5 ml of a 1M sodium bicarbonate solution and 2 ml of acetone was added to the reaction mixture with stirring for 35 minutes. The acetone was distilled off under reduced pressure, and extraction was effected with methylene chloride. The organic phases were dried and concentrated to dryness. The residue was chromatographed on silica under pressure and elution with a methylene chloride-ethyl acetate mixture (75-25) to obtain 602 mg of syn isomer of racemic cis 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-ethoxyimino-acetamido]-3-hydroxymethyl-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-en-2-carboxylate.

Workup

  1. stirringwith stirring for 35 minutes
  2. distillationThe acetone was distilled off under reduced pressure, and extraction
  3. customThe organic phases were dried
  4. concentrationconcentrated to dryness
  5. customThe residue was chromatographed on silica under pressure and elution with a methylene chloride-ethyl acetate mixture (75-25)

Sources & evidence

ORD record
ord-e3a47216f98e4250a9e0fa0e558f5763
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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