Hydrochloric Acid → HCID 54303214, compound

HRID 1770194Notes

Reaction equation

HRID 1770194 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.[ClH:51]>ClCCl.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.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:51])=[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 2

HCID 313Hydrochloric AcidHCID 53865671HCID 53865671, compound

Product 1

HCID 54303214HCID 54303214, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 73974-Toluenesulfonyl chlorideSolvent

Procedure

623 mg of the alcohol of Step F were dissolved in 8 ml of dichloromethane with 834 ml of tosyl chloride, and over 20 minutes, a solution of 534 mg of 4-dimethylamino-pyridine and 5 ml of dichloromethane was added. After stirring for one hour, 2.2 ml of N hydrochloric acid were added with stirring, and after decanting, the organic phase was dried and distilled under reduced pressure. The residue was chromatographed over silica and eluted with dichloromethane-ethyl acetate (9-1) 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 crystallizing from ether.

Workup

  1. stirringwith stirring
  2. customafter decanting
  3. customthe organic phase was dried
  4. distillationdistilled under reduced pressure
  5. customThe residue was chromatographed over silica
  6. washeluted with dichloromethane-ethyl acetate (9-1)

Sources & evidence

ORD record
ord-05b6af40ebb840bcb0b37803e16583a9
Source dataset
uspto-grants-1995_01
Patent number
US05385897

Reaction notes

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