Hydrochloric Acid → HCID 54303214, compound

HRID 1376843Notes

Reaction equation

HRID 1376843 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:48][O:49][CH3:50])[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][C:34]([CH2:46]O)=[C:35]3[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[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:61])(C1C=CC(C)=CC=1)(=O)=O.Cl>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:48][O:49][CH3:50])[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][C:34]([CH2:46][Cl:61])=[C:35]3[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[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

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 53865671HCID 53865671, compound

Product 1

HCID 54303214HCID 54303214, compoundYield 38.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

623 mg of the alcohol of Step F were dissolved in 8 ml of dichloromethane with 834 mg of tosyl chloride and a solution of 534 mg of 4-dimethylamino-pyridine and 5 ml of dichloromethane was introduced over 20 minutes. After 1 hour of stirring, 2.2 ml of N hydrochloric acid were added with stirring and the decanted organic phase was dried and distilled under reduced pressure. The residue was chromatographed on silica and eluted with dichloromethane ethyl acetate (9-1) and crystallized from ether to obtain 245 mg of 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-8-oxo-3-chloromethyl-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate.

Workup

  1. stirringwith stirring
  2. customthe decanted organic phase was dried
  3. distillationdistilled under reduced pressure
  4. customThe residue was chromatographed on silica
  5. washeluted with dichloromethane ethyl acetate (9-1)
  6. customcrystallized from ether

Sources & evidence

ORD record
ord-ca44fb08858f47488b72e085ccc52e12
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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